Tandem alkylation-defluorination reaction: Synthesis of 2-(N-alkyl-N-aryl)amino-3,3-difluoropropenoates from 2-(N-aryl)imino-3,3,3-trifluoropropanoates
1996; Elsevier BV; Volume: 37; Issue: 12 Linguagem: Inglês
10.1016/0040-4039(96)00214-6
ISSN1873-3581
AutoresKenji Uneyama, Fengyang Yan, Susumu Hirama, Toshimasa Katagiri,
Tópico(s)Synthesis and Reactivity of Heterocycles
ResumoA novel synthesis of fluoroolefins from trifluoromethylated compounds with organometallic reagents was developed. The reaction seems to proceed via 1,4-alkylation on imino nitrogen followed by defluorination of the trifluoromethyl group. Diethylzinc was found to be an efficient reagent for the preparation of 2-(N-aryl-N-ethyl)amino-3,3-difluoropropenoates in excellent yield. A similar synthesis of monofluoroolefin with Grignard reagent was also developed.
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