Stereoselective Cycloaddition of Dibenzoxazepinium Ylides to Acetylenes and Fullerene C60. Conformational Behavior of 3-Aryldibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine Sys
详细信息 查看全文
- 作者：Alexander F. Khlebnikov ; Mikhail S. Novikov ; Petr P. Petrovskii ; Alexander S. Konev ; Dmitrii S. Yufit ; Stanislav I. Selivanov ; Holm Frauendorf
- 刊名：Journal of Organic Chemistry
- 出版年：2010
- 出版时间：August 6, 2010
- 年：2010
- 卷：75
- 期：15
- 页码：5211-5215
- 全文大小：838K
- 年卷期：v.75,no.15(August 6, 2010)
- ISSN：1520-6904
文摘
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<sub>60sub> 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<sub>60sub>. Details of cycloaddition and conformational behavior of cycloadducts were studied by DFT computations.