HETEROCYCLES

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■ Heterocycles by Cycloaddition. XII. Cycloaddition-Extrusion of a Mesoionic 1,3-Dithiolium-4-olate and a Mesoionic Oxazolium-5-olate with a Phosphirene. Formation of Six- and Five-membered Heterocycles

Tomoshige Kobayashi, Hidefumi Minemura, and Hiroshi Kato

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto 390-8621, Japan

Abstract

The reaction of a mesoionic dithioliumolate (6) with triphenylphosphirene (7) gave a cycloadduct (8). Pyrolysis of the cycloadduct (8) gave a 1,4-thiaphosphinine (11) and a thiophene (9). Acid treatment or photolysis of the cycloadduct (8) gave the thiophene (9) exclusively. The reaction of a mesoionic oxazolium-5-olate (12) and the phosphirene (7) gave a pyrrole (15) as the only isolable product.