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Communication | Special issue | Vol 28, No. 1, 1989, pp.125-128
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S51
Termal Cycloaddition Reactions of 4,5-Epoxy-4-azahomoadamantanes with Acetylenic 1,3-Dipolarophiles. Novel Formation of 4-Aza-homoadamantano[4,5-a]pyrrole Derivatives

Shoji Eguchi,* Koji Asai, and Tadashgi Sasaki

*Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan

Abstract

Thermal cycloaddition reactions of 5-alkyl-4,5-epoxy-4-azahomoadamantanes 1b-d with dimethyl acetylenedicarboxylate (DMAD) and methyl propiolate afforded 4-azahomoadamantano[4,5-a]pyrrole derivatives 5a-c and 7, while the reaction of the 5-unsubstituted epoxy-4-azahomoadamantane 1a with DMAD gave the oxazoline derivative 4 in a low yield.