Reactions of N-halogenobenzylmethylamines with triethylamine in acetonitrile. Effect of leaving group upon the imine-forming transition state

Bong Rae Cho, Sung Keon Namgoong, Tae Rin Kim

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9 Citations (Scopus)

Abstract

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, kH/kD 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 Cß-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.

Original languageEnglish
Pages (from-to)853-856
Number of pages4
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number7
DOIs
Publication statusPublished - 1987

ASJC Scopus subject areas

  • Chemistry(all)

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