Journal of the American Chemical Society

The β-(Phosphatoxy) alkyl Radical Rearrangement. Rate Constants, Arrhenius Parameters, and Structure Activity Relationships

D Crich, XY Jiao

Index: Crich, David; Jiao, Xian-Yun Journal of the American Chemical Society, 1996 , vol. 118, # 28 p. 6666 - 6670

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Citation Number: 20

Abstract

Rate constants for the migration of a series of p, p-disubstituted β-(diarylphosphatoxy) alkyl migrations have been determined in benzene at reflux by competition against the benzeneselenol clock reaction. There is a strong linear correlation of log (k) with the Hammett σp but not with various σ parameters indicating that the migration occurs through a highly polarized transition state resembling an alkene radical cation loosely bound to a ...