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DOI: 10.1039/A808147F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 509-512

One-pot stereoselective synthesis of trifluoromethylated penta-(2Z,4E[hair space])-dienenitriles via double olefination

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Yanchang Shen, Jiahong Ni, Ping Li and Jie Sun

Abstract

A novel double olefination via sequential transformation of diethyl (1-cyanoethyl)phosphonate and its application to the synthesis of substituted trifluoromethylated pentadienenitriles with 2Z,4E-isomers formed exclusively in 71–85% yield are described. This reaction is of broad scope since R may be alkyl, aryl or a heterocyclic group. The configuration of the products was ascertained on the basis of X-ray crystallographic analysis. The stereochemical results are rationalized by the proposed mechanism.

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