Čeković, Živorad

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  • Čeković, Živorad (11)
  • Čeković, Živorad M. (2)
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Author's Bibliography

Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Saičić, Radomir N.

(Serbian Chemical Society, 2006)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Saičić, Radomir N.
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/259
AB  - The reaction of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I (2) with BF3·Et2O/Bu4NBr can give rise to 4 different products. Each of these products can be obtained selectively, under the appropriate reaction conditions.
AB  - U reakciji α-4(20)-epoksi-5-O-meziltriacetiltaksicina I (2) sa bortrifluorid eteratom i tetrabutilamonijum-bromidom mogu nastati 4 različita proizvoda, u zavisnosti od reakcionih uslova. Svaki od ova 4 proizvoda se može dobiti selektivno, pod odgovarajućim reakcionim uslovima.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr
T1  - Reakcije α-4(20)-epoksi-5-O-meziltriacetiltaksicina I sa tetrabutilamonijum-bromidom u prisustvu bortrifluorid-eterata
VL  - 71
IS  - 7
SP  - 705
EP  - 711
DO  - 10.2298/JSC0607705F
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Saičić, Radomir N.",
year = "2006",
abstract = "The reaction of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I (2) with BF3·Et2O/Bu4NBr can give rise to 4 different products. Each of these products can be obtained selectively, under the appropriate reaction conditions., U reakciji α-4(20)-epoksi-5-O-meziltriacetiltaksicina I (2) sa bortrifluorid eteratom i tetrabutilamonijum-bromidom mogu nastati 4 različita proizvoda, u zavisnosti od reakcionih uslova. Svaki od ova 4 proizvoda se može dobiti selektivno, pod odgovarajućim reakcionim uslovima.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr, Reakcije α-4(20)-epoksi-5-O-meziltriacetiltaksicina I sa tetrabutilamonijum-bromidom u prisustvu bortrifluorid-eterata",
volume = "71",
number = "7",
pages = "705-711",
doi = "10.2298/JSC0607705F"
}
Ferjančić, Z., Matović, R., Čeković, Ž.,& Saičić, R. N.. (2006). Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 71(7), 705-711.
https://doi.org/10.2298/JSC0607705F
Ferjančić Z, Matović R, Čeković Ž, Saičić RN. Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr. in Journal of the Serbian Chemical Society. 2006;71(7):705-711.
doi:10.2298/JSC0607705F .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Saičić, Radomir N., "Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by Bf3·Et2O/Bu4NBr" in Journal of the Serbian Chemical Society, 71, no. 7 (2006):705-711,
https://doi.org/10.2298/JSC0607705F . .
1
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2

Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Jiang, Yi; Snyder, James P.; Trajković, Vladimir; Saičić, Radomir N.

(Oxford : Pergamon-Elsevier Science Ltd, 2006)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Jiang, Yi
AU  - Snyder, James P.
AU  - Trajković, Vladimir
AU  - Saičić, Radomir N.
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2772
AB  - A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid
VL  - 62
IS  - 36
SP  - 8503
EP  - 8514
DO  - 10.1016/j.tet.2006.06.080
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Jiang, Yi and Snyder, James P. and Trajković, Vladimir and Saičić, Radomir N.",
year = "2006",
abstract = "A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. (c) 2006 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid",
volume = "62",
number = "36",
pages = "8503-8514",
doi = "10.1016/j.tet.2006.06.080"
}
Ferjančić, Z., Matović, R., Čeković, Ž., Jiang, Y., Snyder, J. P., Trajković, V.,& Saičić, R. N.. (2006). Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 62(36), 8503-8514.
https://doi.org/10.1016/j.tet.2006.06.080
Ferjančić Z, Matović R, Čeković Ž, Jiang Y, Snyder JP, Trajković V, Saičić RN. Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid. in Tetrahedron. 2006;62(36):8503-8514.
doi:10.1016/j.tet.2006.06.080 .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Jiang, Yi, Snyder, James P., Trajković, Vladimir, Saičić, Radomir N., "Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid" in Tetrahedron, 62, no. 36 (2006):8503-8514,
https://doi.org/10.1016/j.tet.2006.06.080 . .
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14

Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid

Ferjančić, Zorana; Matović, Radomir; Čeković, Živorad; Snyder, James P.; Saičić, Radomir N.

(Oxford : Pergamon-Elsevier Science Ltd, 2005)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Čeković, Živorad
AU  - Snyder, James P.
AU  - Saičić, Radomir N.
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2770
AB  - A C,D-seco-paclitaxel derivative 12 was prepared and tested for biological activity. The key step in the synthesis was a free radical fragmentation of the bicyclic tertiary alcohol 7 under the conditions of the hypobromite reaction. The compound 12 showed no activity in the tubulin test. (c) 2005 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid
VL  - 46
IS  - 30
SP  - 5049
EP  - 5052
DO  - 10.1016/j.tetlet.2005.05.071
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Čeković, Živorad and Snyder, James P. and Saičić, Radomir N.",
year = "2005",
abstract = "A C,D-seco-paclitaxel derivative 12 was prepared and tested for biological activity. The key step in the synthesis was a free radical fragmentation of the bicyclic tertiary alcohol 7 under the conditions of the hypobromite reaction. The compound 12 showed no activity in the tubulin test. (c) 2005 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid",
volume = "46",
number = "30",
pages = "5049-5052",
doi = "10.1016/j.tetlet.2005.05.071"
}
Ferjančić, Z., Matović, R., Čeković, Ž., Snyder, J. P.,& Saičić, R. N.. (2005). Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 46(30), 5049-5052.
https://doi.org/10.1016/j.tetlet.2005.05.071
Ferjančić Z, Matović R, Čeković Ž, Snyder JP, Saičić RN. Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid. in Tetrahedron Letters. 2005;46(30):5049-5052.
doi:10.1016/j.tetlet.2005.05.071 .
Ferjančić, Zorana, Matović, Radomir, Čeković, Živorad, Snyder, James P., Saičić, Radomir N., "Synthesis, biological evaluation, and modeling of a C,D-seco-taxoid" in Tetrahedron Letters, 46, no. 30 (2005):5049-5052,
https://doi.org/10.1016/j.tetlet.2005.05.071 . .
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8

Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III

Saičić, Radomir N.; Matović, Radomir; Čeković, Živorad

(Serbian Chemical Soc, Belgrade, 1999)

TY  - JOUR
AU  - Saičić, Radomir N.
AU  - Matović, Radomir
AU  - Čeković, Živorad
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2777
AB  - From the needles of domestic yew, (Taxus baccata), 10-deacetylbaccatin III (10-DAB) call be isolated in quantities of up to 297 mg per kg of fresh needles. Additional quantities of 10-DAB call be obtained from the extract by NaBH4 mediated reductive hydrolysis of baccatin esters. A four-step procedure converts 10-DAB into taxol in 58% overall yield.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III
VL  - 64
IS  - 9
SP  - 497
EP  - 503
DO  - 10.2298/JSC9909497S
ER  - 
@article{
author = "Saičić, Radomir N. and Matović, Radomir and Čeković, Živorad",
year = "1999",
abstract = "From the needles of domestic yew, (Taxus baccata), 10-deacetylbaccatin III (10-DAB) call be isolated in quantities of up to 297 mg per kg of fresh needles. Additional quantities of 10-DAB call be obtained from the extract by NaBH4 mediated reductive hydrolysis of baccatin esters. A four-step procedure converts 10-DAB into taxol in 58% overall yield.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III",
volume = "64",
number = "9",
pages = "497-503",
doi = "10.2298/JSC9909497S"
}
Saičić, R. N., Matović, R.,& Čeković, Ž.. (1999). Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 64(9), 497-503.
https://doi.org/10.2298/JSC9909497S
Saičić RN, Matović R, Čeković Ž. Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III. in Journal of the Serbian Chemical Society. 1999;64(9):497-503.
doi:10.2298/JSC9909497S .
Saičić, Radomir N., Matović, Radomir, Čeković, Živorad, "Semisynthesis of Taxol (R): an improved procedure far the isolation of 10-deacetylbaccatin III" in Journal of the Serbian Chemical Society, 64, no. 9 (1999):497-503,
https://doi.org/10.2298/JSC9909497S . .
1
2
2

Free radical ring expansion and subsequent reactions of intermediary carbon radicals

Matović, Radomir; Čeković, Živorad

(Serbian Chemical Society, 1996)

TY  - JOUR
AU  - Matović, Radomir
AU  - Čeković, Živorad
PY  - 1996
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2776
AB  - Alkyl radicals, derived from ethyl 1-(bromoalkyl)-2-oxocyclo-alkanecarboxylates or from the corresponding thiohydroxamic esters, undergo a ring expansion reaction and subsequent intermoleculaar addition/elimination reactions. Thus, in the reaction of ethyl 1-(bromomethyl)-2-oxocycloalkanecarboxylates 4 with allytributyltin 5 a ring enlargement for one carbon occurs and by subsequent addition/elimination reactions ethyl 1-allyl-3-oxocycloalkanecarboxylates 6 were obrtained in 45-65% yields. By thermal decomposition of thiohydroxamic esters of ω̄-(1-carbethoxy-2-oxocycloalkyl)-alkanoic acids 13 and 16 a ring expansion for one or three carbon atoms takes place and α,β-unsaturated-γ-keto ester of type 14 and 17, respectively, were obtained in 10-60% yields, accompained with 2-thiazolyl-alkylthio ethers 18.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Free radical ring expansion and subsequent reactions of intermediary carbon radicals
VL  - 61
IS  - 11
SP  - 1095
EP  - 1105
UR  - https://hdl.handle.net/21.15107/rcub_cer_2776
ER  - 
@article{
author = "Matović, Radomir and Čeković, Živorad",
year = "1996",
abstract = "Alkyl radicals, derived from ethyl 1-(bromoalkyl)-2-oxocyclo-alkanecarboxylates or from the corresponding thiohydroxamic esters, undergo a ring expansion reaction and subsequent intermoleculaar addition/elimination reactions. Thus, in the reaction of ethyl 1-(bromomethyl)-2-oxocycloalkanecarboxylates 4 with allytributyltin 5 a ring enlargement for one carbon occurs and by subsequent addition/elimination reactions ethyl 1-allyl-3-oxocycloalkanecarboxylates 6 were obrtained in 45-65% yields. By thermal decomposition of thiohydroxamic esters of ω̄-(1-carbethoxy-2-oxocycloalkyl)-alkanoic acids 13 and 16 a ring expansion for one or three carbon atoms takes place and α,β-unsaturated-γ-keto ester of type 14 and 17, respectively, were obtained in 10-60% yields, accompained with 2-thiazolyl-alkylthio ethers 18.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Free radical ring expansion and subsequent reactions of intermediary carbon radicals",
volume = "61",
number = "11",
pages = "1095-1105",
url = "https://hdl.handle.net/21.15107/rcub_cer_2776"
}
Matović, R.,& Čeković, Ž.. (1996). Free radical ring expansion and subsequent reactions of intermediary carbon radicals. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 61(11), 1095-1105.
https://hdl.handle.net/21.15107/rcub_cer_2776
Matović R, Čeković Ž. Free radical ring expansion and subsequent reactions of intermediary carbon radicals. in Journal of the Serbian Chemical Society. 1996;61(11):1095-1105.
https://hdl.handle.net/21.15107/rcub_cer_2776 .
Matović, Radomir, Čeković, Živorad, "Free radical ring expansion and subsequent reactions of intermediary carbon radicals" in Journal of the Serbian Chemical Society, 61, no. 11 (1996):1095-1105,
https://hdl.handle.net/21.15107/rcub_cer_2776 .
1

Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base

Čeković, Živorad; Matović, Radomir

(Royal Society of Chemistry, 1991)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Matović, Radomir
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2775
AB  - By reaction of 1,4-dibromo-(E)-but-2-ene with dialkyl ketones and sodium hydride the allenic ketones 3 were obtained as the main products, in addition to the symmetrical unsaturated 1,8-diketones 4.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Chemical Communications
T1  - Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base
IS  - 5
SP  - 294
EP  - 295
DO  - 10.1039/C39910000294
ER  - 
@article{
author = "Čeković, Živorad and Matović, Radomir",
year = "1991",
abstract = "By reaction of 1,4-dibromo-(E)-but-2-ene with dialkyl ketones and sodium hydride the allenic ketones 3 were obtained as the main products, in addition to the symmetrical unsaturated 1,8-diketones 4.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Chemical Communications",
title = "Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base",
number = "5",
pages = "294-295",
doi = "10.1039/C39910000294"
}
Čeković, Ž.,& Matović, R.. (1991). Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base. in Journal of the Chemical Society, Chemical Communications
Royal Society of Chemistry.(5), 294-295.
https://doi.org/10.1039/C39910000294
Čeković Ž, Matović R. Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base. in Journal of the Chemical Society, Chemical Communications. 1991;(5):294-295.
doi:10.1039/C39910000294 .
Čeković, Živorad, Matović, Radomir, "Formation of allenes by reaction of 1,4-dibromobut-2-ene with dialkyl ketones and base" in Journal of the Chemical Society, Chemical Communications, no. 5 (1991):294-295,
https://doi.org/10.1039/C39910000294 . .
4
2

Ferrous ion induced decomposition of alkyl hypochlorites

Čeković, Živorad; Đokić, Gordana

(Elsevier, 1981)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Đokić, Gordana
PY  - 1981
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4418
AB  - The decomposition of primary, secondary and tertiary alkyl hypochlorites induced by ferrous and other one-electron oxidizable metal ions leads to δ-chloro alcohols in yields of 34-76%. In decomposition of tertiary alkyl hypochlorites, β-fragmentation competes with intramolecular δ-chlorination. Tertiary cycloalkyl hypochlorites containing five- or six-membered rings undergo β-cleavage giving the corresponding ω-chloro ketones, while 1-methylcycloheptyl and 1-methylcyclooctyl hypochlorites by decomposition with ferrous ion proceed by transannular functionalization of δ-carbon atom and β-cleavage as a competing reaction.
PB  - Elsevier
T2  - Tetrahedron
T1  - Ferrous ion induced decomposition of alkyl hypochlorites
VL  - 37
IS  - 24
SP  - 4263
EP  - 4268
DO  - 10.1016/0040-4020(81)85021-1
ER  - 
@article{
author = "Čeković, Živorad and Đokić, Gordana",
year = "1981",
abstract = "The decomposition of primary, secondary and tertiary alkyl hypochlorites induced by ferrous and other one-electron oxidizable metal ions leads to δ-chloro alcohols in yields of 34-76%. In decomposition of tertiary alkyl hypochlorites, β-fragmentation competes with intramolecular δ-chlorination. Tertiary cycloalkyl hypochlorites containing five- or six-membered rings undergo β-cleavage giving the corresponding ω-chloro ketones, while 1-methylcycloheptyl and 1-methylcyclooctyl hypochlorites by decomposition with ferrous ion proceed by transannular functionalization of δ-carbon atom and β-cleavage as a competing reaction.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Ferrous ion induced decomposition of alkyl hypochlorites",
volume = "37",
number = "24",
pages = "4263-4268",
doi = "10.1016/0040-4020(81)85021-1"
}
Čeković, Ž.,& Đokić, G.. (1981). Ferrous ion induced decomposition of alkyl hypochlorites. in Tetrahedron
Elsevier., 37(24), 4263-4268.
https://doi.org/10.1016/0040-4020(81)85021-1
Čeković Ž, Đokić G. Ferrous ion induced decomposition of alkyl hypochlorites. in Tetrahedron. 1981;37(24):4263-4268.
doi:10.1016/0040-4020(81)85021-1 .
Čeković, Živorad, Đokić, Gordana, "Ferrous ion induced decomposition of alkyl hypochlorites" in Tetrahedron, 37, no. 24 (1981):4263-4268,
https://doi.org/10.1016/0040-4020(81)85021-1 . .
13
15

Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride

Čeković, Živorad; Bošnjak, Jovan; Cvetković, Milutin

(Elsevier, 1980)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Bošnjak, Jovan
AU  - Cvetković, Milutin
PY  - 1980
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4422
AB  - Favorski type rearrangement has been achieved in the lead tetraacetate oxidation of enamines in the presence of boron trifluoride etherate and alcohol.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride
VL  - 21
IS  - 27
SP  - 2675
EP  - 2678
DO  - 10.1016/S0040-4039(00)92837-5
ER  - 
@article{
author = "Čeković, Živorad and Bošnjak, Jovan and Cvetković, Milutin",
year = "1980",
abstract = "Favorski type rearrangement has been achieved in the lead tetraacetate oxidation of enamines in the presence of boron trifluoride etherate and alcohol.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride",
volume = "21",
number = "27",
pages = "2675-2678",
doi = "10.1016/S0040-4039(00)92837-5"
}
Čeković, Ž., Bošnjak, J.,& Cvetković, M.. (1980). Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride. in Tetrahedron Letters
Elsevier., 21(27), 2675-2678.
https://doi.org/10.1016/S0040-4039(00)92837-5
Čeković Ž, Bošnjak J, Cvetković M. Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride. in Tetrahedron Letters. 1980;21(27):2675-2678.
doi:10.1016/S0040-4039(00)92837-5 .
Čeković, Živorad, Bošnjak, Jovan, Cvetković, Milutin, "Favorski type rearrangement in the lead tetraacetate oxidation of enamines promoted by boron trifluoride" in Tetrahedron Letters, 21, no. 27 (1980):2675-2678,
https://doi.org/10.1016/S0040-4039(00)92837-5 . .
11
12

Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides

Čeković, Živorad; Dimitrijević, Lj.; Djokić, G; Srnić, T

(Pergamon Press, 1979)

TY  - JOUR
AU  - Čeković, Živorad
AU  - Dimitrijević, Lj.
AU  - Djokić, G
AU  - Srnić, T
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2752
AB  - By decomposition of alkyl hydroperoxides 1-8 with ferrous sulfate-cupric acetate reagent, intramolecular functionalisation of remote non-activated C atom takes place and unsaturated alcohols with double bond mainly at δ-position are obtained. The reaction proceeds involving the corresponding alkoxy radical 9 and δ-carbon radical 10 as intermediates. One-electron oxidative interception of δ-carbon radical by cupric acetate does not involve the corresponding carbonium ion; instead, the alkyl-copper intermediate 11 is formed and by elimination affords olefinic alcohols. The isotope effect for this elimination process was found to be kh/kd=6.1. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron
T2  - Tetrahedron
T1  - Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides
VL  - 35
IS  - 17
SP  - 2021
EP  - 2026
DO  - 10.1016/S0040-4020(01)88972-9
ER  - 
@article{
author = "Čeković, Živorad and Dimitrijević, Lj. and Djokić, G and Srnić, T",
year = "1979",
abstract = "By decomposition of alkyl hydroperoxides 1-8 with ferrous sulfate-cupric acetate reagent, intramolecular functionalisation of remote non-activated C atom takes place and unsaturated alcohols with double bond mainly at δ-position are obtained. The reaction proceeds involving the corresponding alkoxy radical 9 and δ-carbon radical 10 as intermediates. One-electron oxidative interception of δ-carbon radical by cupric acetate does not involve the corresponding carbonium ion; instead, the alkyl-copper intermediate 11 is formed and by elimination affords olefinic alcohols. The isotope effect for this elimination process was found to be kh/kd=6.1. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron, Tetrahedron",
title = "Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides",
volume = "35",
number = "17",
pages = "2021-2026",
doi = "10.1016/S0040-4020(01)88972-9"
}
Čeković, Ž., Dimitrijević, Lj., Djokić, G.,& Srnić, T.. (1979). Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides. in Tetrahedron
Pergamon Press., 35(17), 2021-2026.
https://doi.org/10.1016/S0040-4020(01)88972-9
Čeković Ž, Dimitrijević L, Djokić G, Srnić T. Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides. in Tetrahedron. 1979;35(17):2021-2026.
doi:10.1016/S0040-4020(01)88972-9 .
Čeković, Živorad, Dimitrijević, Lj., Djokić, G, Srnić, T, "Remote functionalisation by ferrous ion-cupric ion induced decomposition of alkyl hydroperoxides" in Tetrahedron, 35, no. 17 (1979):2021-2026,
https://doi.org/10.1016/S0040-4020(01)88972-9 . .
3
56
50

The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols

Mihailović, Milhailo Lj.; Bošnjak, Jovan; Čeković, Živorad

(Wiley, 1976)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Bošnjak, Jovan
AU  - Čeković, Živorad
PY  - 1976
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4711
AB  - The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified.
PB  - Wiley
T2  - Helvetica Chimica Acta
T1  - The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols
VL  - 59
IS  - 2
SP  - 475
EP  - 486
DO  - 10.1002/hlca.19760590214
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Bošnjak, Jovan and Čeković, Živorad",
year = "1976",
abstract = "The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified.",
publisher = "Wiley",
journal = "Helvetica Chimica Acta",
title = "The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols",
volume = "59",
number = "2",
pages = "475-486",
doi = "10.1002/hlca.19760590214"
}
Mihailović, M. Lj., Bošnjak, J.,& Čeković, Ž.. (1976). The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols. in Helvetica Chimica Acta
Wiley., 59(2), 475-486.
https://doi.org/10.1002/hlca.19760590214
Mihailović ML, Bošnjak J, Čeković Ž. The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols. in Helvetica Chimica Acta. 1976;59(2):475-486.
doi:10.1002/hlca.19760590214 .
Mihailović, Milhailo Lj., Bošnjak, Jovan, Čeković, Živorad, "The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols" in Helvetica Chimica Acta, 59, no. 2 (1976):475-486,
https://doi.org/10.1002/hlca.19760590214 . .
6
6

Oxidation and reduction of phenols

Mihailović, Mihailo; Čeković, Živorad

(wiley, 1971)

TY  - CHAP
AU  - Mihailović, Mihailo
AU  - Čeković, Živorad
PY  - 1971
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/760
PB  - wiley
T2  - Patai Chemistry of the Functional Groups: Chemistry of the Hydroxil Group
T1  - Oxidation and reduction of phenols
SP  - 505
EP  - 592
DO  - 10.1002/9780470771259.ch10
ER  - 
@inbook{
author = "Mihailović, Mihailo and Čeković, Živorad",
year = "1971",
publisher = "wiley",
journal = "Patai Chemistry of the Functional Groups: Chemistry of the Hydroxil Group",
booktitle = "Oxidation and reduction of phenols",
pages = "505-592",
doi = "10.1002/9780470771259.ch10"
}
Mihailović, M.,& Čeković, Ž.. (1971). Oxidation and reduction of phenols. in Patai Chemistry of the Functional Groups: Chemistry of the Hydroxil Group
wiley., 505-592.
https://doi.org/10.1002/9780470771259.ch10
Mihailović M, Čeković Ž. Oxidation and reduction of phenols. in Patai Chemistry of the Functional Groups: Chemistry of the Hydroxil Group. 1971;:505-592.
doi:10.1002/9780470771259.ch10 .
Mihailović, Mihailo, Čeković, Živorad, "Oxidation and reduction of phenols" in Patai Chemistry of the Functional Groups: Chemistry of the Hydroxil Group (1971):505-592,
https://doi.org/10.1002/9780470771259.ch10 . .
19
11

Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight

Mihailović, Milhailo Lj.; Maksimović, Z.; Jeremić, Dragoslav; Čeković, Živorad M.; Milovanović, Aleksandar Ž.; Lorenc, Ljubinka B.

(Elsevier, 1965)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Maksimović, Z.
AU  - Jeremić, Dragoslav
AU  - Čeković, Živorad M.
AU  - Milovanović, Aleksandar Ž.
AU  - Lorenc, Ljubinka B.
PY  - 1965
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4542
AB  - The action of lead tetraacetate on ethanol, 1-propanol, 2-propanol and 2-butanol has been studied under various experimental conditions, and it was found that the tetravalent lead compound reacts with alcohols in ways not so far observed. The possible reaction schemes are discussed in terms of homolytic and heterolytic cleavage of the intermediate alkoxy lead acetate complexes.
PB  - Elsevier
T2  - Tetrahedron
T1  - Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight
VL  - 21
IS  - 6
SP  - 1395
EP  - 1410
DO  - 10.1016/S0040-4020(01)98301-2
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Maksimović, Z. and Jeremić, Dragoslav and Čeković, Živorad M. and Milovanović, Aleksandar Ž. and Lorenc, Ljubinka B.",
year = "1965",
abstract = "The action of lead tetraacetate on ethanol, 1-propanol, 2-propanol and 2-butanol has been studied under various experimental conditions, and it was found that the tetravalent lead compound reacts with alcohols in ways not so far observed. The possible reaction schemes are discussed in terms of homolytic and heterolytic cleavage of the intermediate alkoxy lead acetate complexes.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight",
volume = "21",
number = "6",
pages = "1395-1410",
doi = "10.1016/S0040-4020(01)98301-2"
}
Mihailović, M. Lj., Maksimović, Z., Jeremić, D., Čeković, Ž. M., Milovanović, A. Ž.,& Lorenc, L. B.. (1965). Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight. in Tetrahedron
Elsevier., 21(6), 1395-1410.
https://doi.org/10.1016/S0040-4020(01)98301-2
Mihailović ML, Maksimović Z, Jeremić D, Čeković ŽM, Milovanović AŽ, Lorenc LB. Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight. in Tetrahedron. 1965;21(6):1395-1410.
doi:10.1016/S0040-4020(01)98301-2 .
Mihailović, Milhailo Lj., Maksimović, Z., Jeremić, Dragoslav, Čeković, Živorad M., Milovanović, Aleksandar Ž., Lorenc, Ljubinka B., "Reactions with lead tetraacetate-IV. Oxidation of saturated aliphatic alcohols-II; Alcohols of low molecular weight" in Tetrahedron, 21, no. 6 (1965):1395-1410,
https://doi.org/10.1016/S0040-4020(01)98301-2 . .
28
8

Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols

Mihailović, Milhailo Lj.; Čeković, Živorad M.; Maksimović, Z.; Jeremić, Dragoslav; Lorenc, Ljubinka B.; Mamuzić, R. I.

(Elsevier, 1965)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Čeković, Živorad M.
AU  - Maksimović, Z.
AU  - Jeremić, Dragoslav
AU  - Lorenc, Ljubinka B.
AU  - Mamuzić, R. I.
PY  - 1965
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4553
AB  - The action of lead tetraacetate, in benzene solution, on various unbranched primary and secondary aliphatic alcohols containing 4 to 12 carbon atoms has been investigated and the ratio of carbonyl compounds, cyclic ethers and fragmentation products determined. The results obtained are discussed with regard to the number and length of the n-alkyl rests attached to the carbinol carbon atom of the starting alcohol.
PB  - Elsevier
T2  - Tetrahedron
T1  - Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols
VL  - 21
IS  - 10
SP  - 2799
EP  - 2812
DO  - 10.1016/S0040-4020(01)98365-6
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Čeković, Živorad M. and Maksimović, Z. and Jeremić, Dragoslav and Lorenc, Ljubinka B. and Mamuzić, R. I.",
year = "1965",
abstract = "The action of lead tetraacetate, in benzene solution, on various unbranched primary and secondary aliphatic alcohols containing 4 to 12 carbon atoms has been investigated and the ratio of carbonyl compounds, cyclic ethers and fragmentation products determined. The results obtained are discussed with regard to the number and length of the n-alkyl rests attached to the carbinol carbon atom of the starting alcohol.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols",
volume = "21",
number = "10",
pages = "2799-2812",
doi = "10.1016/S0040-4020(01)98365-6"
}
Mihailović, M. Lj., Čeković, Ž. M., Maksimović, Z., Jeremić, D., Lorenc, L. B.,& Mamuzić, R. I.. (1965). Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols. in Tetrahedron
Elsevier., 21(10), 2799-2812.
https://doi.org/10.1016/S0040-4020(01)98365-6
Mihailović ML, Čeković ŽM, Maksimović Z, Jeremić D, Lorenc LB, Mamuzić RI. Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols. in Tetrahedron. 1965;21(10):2799-2812.
doi:10.1016/S0040-4020(01)98365-6 .
Mihailović, Milhailo Lj., Čeković, Živorad M., Maksimović, Z., Jeremić, Dragoslav, Lorenc, Ljubinka B., Mamuzić, R. I., "Lead tetraacetate oxidation of saturated aliphatic alcohols.-III. Unbranched primary and secondary alcohols" in Tetrahedron, 21, no. 10 (1965):2799-2812,
https://doi.org/10.1016/S0040-4020(01)98365-6 . .
48
37