Polylithiumorganic compounds-21. 1 on the deprotonation of 1-and 3-phenylpropyne as well as phenylallene with butyllithium. A reinvestigation: Three different …

A Maercker, J Fischenich

Index: Maercker, Adalbert; Fischenich, Jakob Tetrahedron, 1995 , vol. 51, # 37 p. 10209 - 10218

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Citation Number: 12

Abstract

In contrast to the literature, with butyllithium only one and the same dianion—namely 7-is formed starting with each of the three hydrocarbons 1, 4, and 6. On the other hand, upon working at low temperature in tetrahydrofuran as the solvent we were able to detect the three corresponding monoanions 9, 15, and 16, most interestingly 15 and 16 at temperatures higher than− 40° C show rearrangement with 1, 3-hydrogen shift.