98760-23-7Relevant academic research and scientific papers
Reactions of N-Halogenobenzylmethylamines with Triethylamine in Acetonitrile. Effect of Leaving Group upon the Imine-forming Transition State
Cho, Bong Rae,Namgoong, Sung Keon,Kim, Tae Rin
, p. 853 - 856 (2007/10/02)
Reactions of N-halogenobenzylmethylamines (1) and (2) with Et3N-MeCN have been investigated kinetically.Eliminations from (1) and (2) were quantitative and regiospecific, producing only benzylidenemethylamines.For the elimination reaction of (1) with Et3N, kH/kD 5.7, ρ 0.88, 9.1 kcal mol-1, and -42.4 cal mol-1 K-1 were determined.The transition-state structure is assessed as being highly symmetric with similar extents of Cβ-H and Nα-Cl bond cleavage, little carbanionic character, and significant ?-bond formation.The structure of the transition state changes only slightly with the change in the leaving group from Cl to Br.
