Abstract
Abstract Peri- and stereoselective cycloadducts were obtained from the reactions of 8-aryl-8-azaheptafulvenes with some sulfenes. 8-Aryl-8-azaheptafulvenes reacted with phenylsulfene to give cis [8+2] cycloadducts as the sole products which would have resulted either from the endo approach or via the endo intermediate of the two reagents. On the other hand, with benzoylsulfene trans [8+2] cycloadducts were isolated. The formation of the latter products was rationalized by considering epimerization of the initially formed cis adducts. The cis [8+2] cycloadducts to vinylsulfene did not give the trans isomers but the hydrogen migrated derivatives under the influence of bases. The mechanism of the above reactions is also discussed.
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