Hydroxyacetals, phthalans, and isobenzofurans therefrom

BA Keay, HP Plaumann, D Rajapaksa…

Index: Keay, Brian A.; Plaumann, Heinz P.; Rajapaksa, Dayananda; Rodrigo, Russell Canadian Journal of Chemistry, 1983 , vol. 61, p. 1987 - 1995

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Citation Number: 37

Abstract

A general method for the generation of isobenzofuran intermediates is described. Lithiated aromatic acetals are converted to hydroxyacetals (A) which may be cyclized to isobenzofurans by mild acid treatment through the 1-hydroxyphthalans (B). The isobenzofurans generated in situ are trapped by a variety of dienophiles to provide the expected oxo-bicyclo adducts (C). The mass and 1Hmr spectra of B and C are discussed.