Carbenoid chain reactions: Substitutions by organolithium compounds at unactivated 1-chloro-1-alkenes

…, C Behringer, T Menke, J Freudenreich…

Index: Knorr, Rudolf; Pires, Claudio; Behringer, Claudia; Menke, Thomas; Freudenreich, Johannes; Rossmann, Eva C.; Boehrer, Petra Journal of the American Chemical Society, 2006 , vol. 128, # 46 p. 14845 - 14853

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Citation Number: 24

Abstract

The deceptively simple “cross-coupling” reactions Alk2C CA-Cl+ RLi→ Alk2C CA-R+ LiCl (A= H, D, or Cl) occur via an alkylidenecarbenoid chain mechanism in three steps without a transition metal catalyst. In the initiating step 1, the sterically shielded 2-(chloromethylidene)- 1, 1, 3, 3-tetramethylindans 2a-c (Alk2C CA-Cl) generate a Cl, Li-alkylidenecarbenoid (Alk2C CLi-Cl, 6) through the transfer of atom A to RLi (methyllithium, n-butyllithium, or ...