Solvolytic generation of. alpha.-sulfonyl and. alpha.-sulfinyl carbocations

X Creary, ME Mehrsheikh-Mohammadi…

Index: Creary, Xavier; Mehrsheikh-Mohammadi, M.E.; Eggers, Mark D. Journal of the American Chemical Society, 1987 , vol. 109, # 8 p. 2435 - 2442

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Citation Number: 18

Abstract

Abstract: A series of mesylates of general type ArC (CH3)(S02Ph) OMs, 14, have been prepared and studied under solvolytic conditions. The Hammett p value in methanol is-7.98. A solvent effect study on 14b, where Ar= p-CH3C6H4, gave a good correlation with YoTS values and an m value of 0.85. These data were interpreted in terms of the involvement of a- sulfonyl-substituted carbocations, which have a large demand for aryl group stabilization. ...