Reactions of phthalans with dienophiles. I. Synthesis of naphthalenes from phthalans and activated acetylenes
- 1 December 1980
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 58 (23) , 2573-2579
- https://doi.org/10.1139/v80-410
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.Keywords
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