Reactions of N-halogenobenzylmethylamines (1) and (2) with Et 3N-MeCN have been investigated kinetically. Eliminations from (1) and (2) were quantitative and regiospecific, producing only benzylidenemethylamines. For the elimination reaction of (1) with Et 3N, k H/k D 5.7, ρ 0.88, ΔH‡ 9.1 kcal mol -1, and ΔS‡ -42.4 cal mol -1 K -1 were determined. The transition-state structure is assessed as being highly symmetric with similar extents of C ß-H and N α-Cl bond cleavage, little carbanionic character, and significant π-bond formation. The structure of the transition state changes only slightly with the change in the leaving group from Cl to Br.
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 2|
|Publication status||Published - 1987 Dec 1|
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