Solvolytic elimination reactions of tertiary. alpha.-CSNMe2-substituted systems

…, HN Hatoum, A Barton, TE Aldridge

Index: Creary, Xavier; Hatoum, Holia N.; Barton, Angela; Aldridge, Timothy E. Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1887 - 1897

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Citation Number: 24

Abstract

The tertiary benzylic a-CSNMez-substituted p-nitrobenzoates and trifluoroacetates of general structure Ar (CH3) C (CSNMe2)(OCOR), 7 and 8, solvolyze to give exclusively elimination producb HzC= C (CSNMe2) Ar. A Hammett study gave a nonlinear correlation. Variation in rate with solvent ionizing power was small for the unsubstituted trifluoroacetate derivative of 8, and the &CD3 isotope effect on rate was negligible. There is, however, a ...