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■ Synthesis and Properties of Derivatives of Cyclopenta[b]pyran and Cyclopenta[b]thiapyran Isoelectronic with Azulene

Masahiko Iyoda, Yoshio Aso, and Masazumi Nakagawa*

*Department of Chemistry, Faculty of Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

Abstract

Cyclopenta[b]pyran and cyclopenta[b]thiapyran derivatives isoelectronic with azulene have been synthesized by intramolecular cyclization of substituted octadienyne-dials. The cyclization reaction of octadienyne-dials proceeds regiospecifically and the formation of cyclopenta[b]pyrans and/or cyclopenta[b]thiapyrans depends on a subtle variety of the reaction conditions.