133205-43-3Relevant academic research and scientific papers
Synthesis and reactivity of 3-chloro-3-trifluoromethylacroleins: stabilisation of the tetrahedral intermediate in a nucleophilic vinylic "substitution"
Alvernhe, Gerard,Greif, Dieter,Langlois, Bernard,Laurent, Andre,Drean, Isabelle Le,et al.
, p. 167 - 172 (2007/10/02)
Trifluoromethyl ketones 1a-d reacted with the Vilsmeier reagent to give CF3-substituted β-chloro-vinylaldehydes 2a-d in good yields.Using 2-amino-ethanethiol as a nucleophile, a different regiochemistry of cyclization that depends on a methyl or trifluoromethyl substituent was observed.The cyclization of trifluoromethyl compounds 2a and 2e into thiazolidines 7 or 24 results in the stabilization of the tetrahedral intermediate by the captodative effect.We report the first direct substitution of a tetrahedral intermediate (instead of elimination) in a nucleophilic vinylic reaction. trifluoromethylacroleins / Michael addition / tetrahedral intermediate
Synthesis of β-chloro(trifluoromethyl)acroleins and a specific reaction towards β-aminothiols
Alvernhe, Gerard,Langlois, Bernard,Laurent, Andre,Le Drean, Isabelle,Selmi, Abdelaziz,Weissenfels, Menfred
, p. 643 - 646 (2007/10/02)
β-chloro-β-(trifluoromethyl)acroleins and β-chloro-α-(trifluoromethyl)-acrolein have been synthesized through Vilsmeier's reaction. A specific 1,4-addition of the nitrogen atom from β-aminothiols is observed.
