Free radical ring expansion and subsequent reactions of intermediary carbon radicals
Apstrakt
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.
Ključne reči:
Allytributyltin / Free radicals / Ring expension / Thiohydroxamic estersIzvor:
Journal of the Serbian Chemical Society, 1996, 61, 11, 1095-1105Izdavač:
- Serbian Chemical Society
Institucija/grupa
IHTMTY - 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 .