Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60
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2018
Authors
Pavlovic, Radoslav Z.Mitrović, Aleksandra
Coldren, William H.
Bjelaković, Mira
Hadad, Christopher M.
Maslak, Veselin R.
Milić, Dragana
Article (Published version)
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The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.
Source:
Journal of Organic Chemistry, 2018, 83, 4, 2166-2172Publisher:
- American Chemical Society (ACS)
Funding / projects:
- Design, synthesis and investigations of fullerene based nanomolecular machines (RS-MESTD-Basic Research (BR or ON)-172002)
Note:
- Supporting information: https://cer.ihtm.bg.ac.rs/handle/123456789/4504
Related info:
- Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4504
DOI: 10.1021/acs.joc.7b03083
ISSN: 0022-3263
PubMed: 29359560
WoS: 000427094200049
Scopus: 2-s2.0-85042184414
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IHTMTY - JOUR AU - Pavlovic, Radoslav Z. AU - Mitrović, Aleksandra AU - Coldren, William H. AU - Bjelaković, Mira AU - Hadad, Christopher M. AU - Maslak, Veselin R. AU - Milić, Dragana PY - 2018 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2323 AB - The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts. PB - American Chemical Society (ACS) T2 - Journal of Organic Chemistry T1 - Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60 VL - 83 IS - 4 SP - 2166 EP - 2172 DO - 10.1021/acs.joc.7b03083 ER -
@article{ author = "Pavlovic, Radoslav Z. and Mitrović, Aleksandra and Coldren, William H. and Bjelaković, Mira and Hadad, Christopher M. and Maslak, Veselin R. and Milić, Dragana", year = "2018", abstract = "The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.", publisher = "American Chemical Society (ACS)", journal = "Journal of Organic Chemistry", title = "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60", volume = "83", number = "4", pages = "2166-2172", doi = "10.1021/acs.joc.7b03083" }
Pavlovic, R. Z., Mitrović, A., Coldren, W. H., Bjelaković, M., Hadad, C. M., Maslak, V. R.,& Milić, D.. (2018). Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry American Chemical Society (ACS)., 83(4), 2166-2172. https://doi.org/10.1021/acs.joc.7b03083
Pavlovic RZ, Mitrović A, Coldren WH, Bjelaković M, Hadad CM, Maslak VR, Milić D. Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry. 2018;83(4):2166-2172. doi:10.1021/acs.joc.7b03083 .
Pavlovic, Radoslav Z., Mitrović, Aleksandra, Coldren, William H., Bjelaković, Mira, Hadad, Christopher M., Maslak, Veselin R., Milić, Dragana, "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60" in Journal of Organic Chemistry, 83, no. 4 (2018):2166-2172, https://doi.org/10.1021/acs.joc.7b03083 . .