133205-46-6

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 119197-24-9 3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 

Relevant academic research and scientific papers

Trifluoromethyl Substitution Affects the Regiochemistry of Cyclising Condensation in 1,4 Substitution Processes

β-Trifluoromethyl β-chloroacrolein 2 reacts with 2-mercaptoethylamine 3 to produce thiazolidine 5 instead of the expected thiazepine 8.The reason of this behaviour is the formation of the tetrahedral intermediate 6 because of stabilisation by the trifluoromethyl group; an intramolecular substitution takes place faster than a 1,4 addition-elimination process. Key Words: Trifluoromethyl; Michael reaction; regiochemistry; thiazolidine; thiazepine

Synthesis and reactivity of 3-chloro-3-trifluoromethylacroleins: stabilisation of the tetrahedral intermediate in a nucleophilic vinylic "substitution"

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

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.