Photochemical transformations. 48. The nonconcertedness of nucleofuge loss and anti-aryl migration in photochemical Wagner-Meerwein rearrangements

SJ Cristol, MB Ali, IV Sankar

Index: Cristol, Stanley J.; Ali, Mahfuza B.; Sankar, Iyer V. Journal of the American Chemical Society, 1989 , vol. 111, # 21 p. 8207 - 8211

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Citation Number: 8

Abstract

Abstract: Preparation of the two diastereomers of 3-(3, 5-dimethoxyphenyl)-2-butanol and of their 2-deuterio analogues has been carried out. When the methanesulfonate esters of the diastereomers were solvolyzed by heating at reflux in 50% aqueous methanol, the resulting alcohols and methyl ethers were formed with complete retention of diastereomeric identity and without measurable hydride migration to give the 2-aryl-2-butyl isomer. Similar ...