Journal of the Chemical Society. Perkin transactions I p. 1369 - 1373 (1991)
Update date:2022-08-03
Topics:
Weiyu, Ding
Jiaqi, Pu
Chunming, Zhang
Weiguo, Cao
The stereoselective synthesis of (Z)-methyl 3-perfluoroalkyl-4-substituted-phenylbut-3-enoates 8a-o has been investigated.The reaction of substituted benzyltriphenylphosphonium bromides 5a-e with methyl 2-perfluoroalkylnoates 2a-c in the presence of K2CO3 at room temp. gives two adducts, methyl 3-perfluoroalkyl-4-substituted-phenyl-2-triphenylphosphoranylidenebut-3-enoates, 6a-o and methyl 3-perfluoroalkyl-4-substituted-phenyl-4-triphenylphosphoranylidenebut-2-enoates, 7a-o.Compounds 6a-o exist as pairs of E/Z isomers, the ratios are 2:1 for RF = CF3, and 3:1 for RF = C2F5 or C3F7.Compounds 7a-o are transformed into 6a-o when heated. (Z)-Methyl 3-perfluoroalkyl-4-substituted-phenylbut-3-enoates 8a-o can be obtained stereoselectively in high yield when an aqueous methanol solution of mixed 6a-o and 7a-o was heated for 10-20 h.
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