Reactions of phthalans with dienophiles. I. Synthesis of naphthalenes from phthalans and activated acetylenes

Author:

Contreras Luis,MacLean David B.

Abstract

Diethoxyphthalans and activated acetylenes react at temperatures of 140–160 °C to yield substituted naphthalenes. It is proposed that the reaction occurs through the intermediacy of 1-ethoxyisobenzofurans generated thermally from the phthalans. The transient 1-ethoxyisobenzofurans are postulated to add to the acetylenes in a cycloaddition reaction to yield tricyclic intermediates that are transformed to naphthalenes at the elevated temperature of the reaction. Reactions with unsymmetrical acetylenes provided information on the regioselectivity of the reaction.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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