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
2010 | journal article. A publication with affiliation to the University of Göttingen.
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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
Khlebnikov, A. F.; Novikov, M. S.; Petrovskii, P. P.; Konev, A. S.; Yufit, D. S.; Selivanov, S. I. & Frauendorf, H. (2010)
The Journal of Organic Chemistry, 75(15) pp. 5211-5215. DOI: https://doi.org/10.1021/jo100966j
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Details
- Authors
- Khlebnikov, Alexander F.; Novikov, Mikhail S.; Petrovskii, Petr P.; Konev, Alexander S.; Yufit, Dmitry S.; Selivanov, Stanislav I.; Frauendorf, Holm
- Abstract
- 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.
- Issue Date
- 2010
- Status
- published
- Publisher
- Amer Chemical Soc
- Journal
- The Journal of Organic Chemistry
- ISSN
- 0022-3263
