Mechanism of the Stevens rearrangement of ammonium ylides

Y Maeda, Y Sato

Index: Maeda, Yasuhiro; Sato, Yoshiro Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 10 p. 1491 - 1493

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Citation Number: 24

Abstract

Isomerization of trimethylammonium N-benzylide 2 failed to occur at room temperature in a non-basic medium (HMPA) or at-78° C in the presence of butyllithium in THF. However, N, N- dimethyl-1-phenylethylamine 4 (Stevens rearrangement product) was formed when the temperature of the latter reaction was raised to room temperature. The mechanism of the Stevens rearrangement is discussed.