Novel nucleophilic substitution reaction by radical cation intermediates. Photosensitized transacetalization via SON1 mechanism

S Hashimoto, I Kurimoto, Y Fujii…

Index: Hashimoto, S.; Kurimoto, I.; Fujii, Y.; Noyori, R. Journal of the American Chemical Society, 1985 , vol. 107, # 5 p. 1427 - 1429

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Citation Number: 22

Abstract

DCNB: p-dicyanobenzene tertiary alcohol or weakly nucleophilic phenol was employed, 3, 4- dihydro-2H-pyran was formed as a major byprod~ ct.~ The stereochemistry of the transacetalization is to be noted. When irradiation of an equimolar mixture of cis-or trans-6- methyltetrahydropyran-2-yl ether 4 and an alcohol was conducted