Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60 . Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems
Тип публикации: Journal Article
Дата публикации: 2010-07-06
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
20604511
Organic Chemistry
Краткое описание
Cycloaddition of dibenzoxazepinium ylides to acetylene carboxylates leads to cis-3-aryl-3,13b-dihydrodibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepinecarboxylates, which smoothly dehydrogenate to the corresponding pyrrole derivatives. The o-bromophenyl-substituted pyrrole, in contrast to the pyrroline analogue, demonstrates atropoisomerism. Stereoselective cycloaddition of dibenzoxazepinium ylides to fullerene C(60) gives rise to fulleropyrrolidines with cis-configuration. Restricted Ph group rotation is found in the phenyl derivative. Only one of two possible atropoisomers is formed in the reaction of o-bromophenyl-substituted ylide with fullerene C(60). Details of cycloaddition and conformational behavior of cycloadducts were studied by DFT computations.
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Khlebnikov A. F. et al. Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60. Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems // Journal of Organic Chemistry. 2010. Vol. 75. No. 15. pp. 5211-5215.
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Khlebnikov A. F., Novikov M. S., Petrovskii P. P., Konev A. S., Yufit D. S., Selivanov S. I., Frauendorf H. Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60. Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems // Journal of Organic Chemistry. 2010. Vol. 75. No. 15. pp. 5211-5215.
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TY - JOUR
DO - 10.1021/jo100966j
UR - https://doi.org/10.1021/jo100966j
TI - Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60. Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems
T2 - Journal of Organic Chemistry
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
AU - Petrovskii, Petr P
AU - Konev, Alexander S.
AU - Yufit, Dmitrii S.
AU - Selivanov, Stanislav I
AU - Frauendorf, Holm
PY - 2010
DA - 2010/07/06
PB - American Chemical Society (ACS)
SP - 5211-5215
IS - 15
VL - 75
PMID - 20604511
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2010_Khlebnikov,
author = {Alexander F Khlebnikov and Mikhail S. Novikov and Petr P Petrovskii and Alexander S. Konev and Dmitrii S. Yufit and Stanislav I Selivanov and Holm Frauendorf},
title = {Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60. Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems},
journal = {Journal of Organic Chemistry},
year = {2010},
volume = {75},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jo100966j},
number = {15},
pages = {5211--5215},
doi = {10.1021/jo100966j}
}
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Khlebnikov, Alexander F., et al. “Stereoselective cycloaddition of dibenzoxazepinium ylides to acetylenes and fullerene C 60. Conformational behavior of 3-aryldibenzo[ b, f ]pyrrolo[1,2- d ][1,4]oxazepine systems.” Journal of Organic Chemistry, vol. 75, no. 15, Jul. 2010, pp. 5211-5215. https://doi.org/10.1021/jo100966j.
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