Inductive enhancement of aryl participation

JB Lambert, HW Mark, ES Magyar

Index: Lambert,J.B. et al. Journal of the American Chemical Society, 1977 , vol. 99, # 9 p. 3059 - 3067

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Citation Number: 26

Abstract

Abstract: Enhanced participation by an aryl group in solvolysis can be achieved by placing an electron-withdrawing substituent vicinal to the leaving group. We have examined the acetolysis of meso-1, 4-diaryl-2, 3-butyl ditosylates (3) and of 1, 4-diaryl-2-butyl tosylates (4), in which the aryl groups are substituted with p-OCH3, p-CH3, H, p-C1, m-CF3, and p-NOz. The second tosylate group provides the inductive stimulus For increased aryl participation. ...

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