Azetidines. 5. Reaction of 1, 1, 3, 3-tetramethyl-and 1-benzyl-1, 3, 3-trimethylazetidinium ions with butyllithium and phenyllithium. Deuterium labeling as a mechanistic …

…, IE Wills, L Von Dollen, BL Butler, J Porter…

Index: Wills, Max T.; Wills, Irene E.; Dollen, Lawrence Von; Butler, Barry L.; Porter, John; Anderson, Arthur G. Journal of Organic Chemistry, 1980 , vol. 45, # 12 p. 2489 - 2498

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Citation Number: 13

Abstract

With phenyllithium, 1 gave 2 and l-(dimethylamino)-2, 2-dimethyl-3-phenylpropane (11). With butyllithium, 7 gave 2-phenyl-1, 4, 4-trimethylpyrrolidine (S), l-benzyl-3, 3- dimethylpyrrolidine (9), and 1-neopentyl-2-phenylpyrrolidine (10). The reaction of phenyllithium with 7 gave only 8 and 9. Mechanistic information was obtained by labeling 1 with deuterium in three different ways: N-methyl-d3, 2, 2-d2, and N-methyl-d3-2, 2-d2. A ...