Journal of the American Chemical Society

The ortho-Claisen Rearrangement. IV. The Rearrangement of X-Cinnamyl p-Tolyl Ethers1

WN White, WK Fife

Index: White,W.N.; Fife,W.K. Journal of the American Chemical Society, 1961 , vol. 83, p. 3846 - 3853

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Citation Number: 53

Abstract

The rates of rearrangement of ten X-cinnamyl p-tolyl ethers were determined with the object of obtaining information to define the electronic character of the traiisition state of the Claisen rearrangement. The rates were best correlated by u+-constants and a p-value of-0.40. Since the rates of rearrangement of allyl PX-phenyl ethers are similarly correlated by negative p- and u+-constants, the transition state must involve a depletion of electrons in both the aryl ...