Photoinduced Alkoxylation of 2-Vinylpyridinium Ion.

A Ishida, T Uesugi, S Takamuku

Index: Ishida, Akito; Uesugi, Tatsumi; Takamuku, Setsuo Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 5 p. 1580 - 1582

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Citation Number: 5

Abstract

Photoirradiation of 2-vinylpyridine in acidic methanol afforded methyl 2-(2-pyridyl) ethyl ether in a high yield. Reactions in acidic ethanol and 2-propanol also provided the corresponding alkoxyl derivatives along with a considerable amount of 2-ethylpyridine. It was suggested that photoinduced intramolecular charge-shift from the pyridinium ion moiety into the vinyl group initiates the regioselective nucleophilic addition of alcohol.