Research News, Jun 12th, 2012

    Synthesis of gem-dihaloenynes and butatrienes from gem-dihalovinyl derivatives

 
Tianhao Meng, Hui-Jun Zhang, and Zhenfeng Xi*

Tetrahedron Lett. 2012, Accepted.

gem-Dihaloenynes are useful building blocks. Butatrienes are structurally interesting compounds. Synthetic methods for such compounds are very limited.

In recent years, we have been interested in the preparation and synthetic applications of polyhalo compounds including gem-dihalo vinylic moieties, aiming at utilizing the potential synergistic effect among functional groups on conjugated systems. As our continued interest in the synthetic applications of such polyhalo-substituted conjugated systems, we subjected such compounds under the Fritsch-Buttenberg-Wiechell (FBW) rearrangement conditions. In this paper, we report efficient synthesis of both gem-dihaloenynes and butatrienes via lithiation-promoted transformation of 1,1,4,4-tetrahalo 1,3-butadienes and gem-dihalovinyl derivatives.