The E2C mechanism in elimination reactions. 8. Interaction of conjugating substituents with E2C- and E2H-like transition states
Muir, D.M. and Parker, A.J. (1976) The E2C mechanism in elimination reactions. 8. Interaction of conjugating substituents with E2C- and E2H-like transition states. The Journal of Organic Chemistry, 41 (19). pp. 3201-3204.
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Rates and olefinic products of dehydrotosylation of secondary tosylates under conditions suitable for E2C, E2H, and solvolysis (El) reactions, respectively, have been measured. The kinetic products are compared with those from equilibration. Quite different proportions of olefins are obtained according to the reaction conditions and this has obvious value for synthetic work. The tosylates studied contain groups, e.g., phenyl, acyl, viny1, capable of conjugating with the developing double bond in the transition state leading to olefins. The product distribution from E2Clike reactions is not entirely consistent with the concept of a very product- (olefin-) like E2C transition state.
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