Starting with 1,1,1-trifluoroacetone, 3-(trifluoromethyl)-1-(trimethylsilyloxy)-1,3-butadiene has been prepd. as a mixt. of (Z) and (E) isomers. The diene undergoes [4 + 2] cycloaddn. reactions with a variety of dienophiles affording trifluoromethyl-substituted carbocyclic and heterocyclic compds. in yields ranging from moderate to good. [on SciFinder (R)]
Title
The Diels-Alder route to trifluoromethyl-substituted carbo- and heterocycles
Published in
Liebigs Annalen
Issue
9
Pages
1587-9
Date
1995
Note
CAN 124:55071 21-2 General Organic Chemistry Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0947-3440 written in English. 421-50-1 (1,1,1-Trifluoroacetone); 545-06-2 (Trichloroacetonitrile); 623-47-2 (Ethyl propiolate); 670-54-2 (TCNE); 762-42-5 (Dimethyl acetylenedicarboxylate); 7020-80-6; 7206-05-5; 23521-49-5 Role: RCT (Reactant), RACT (Reactant or reagent) (Diels-Alder route to trifluoromethyl-substituted carbo- and heterocycles); 103313-68-4P; 128722-19-0P; 172264-38-9P; 172264-39-0P; 172264-40-3P; 172264-41-4P; 172264-42-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (Diels-Alder route to trifluoromethyl-substituted carbo- and heterocycles); 583-02-8P; 728-47-2P; 172264-43-6P; 172264-44-7P; 172264-45-8P Role: SPN (Synthetic preparation), PREP (Preparation) (Diels-Alder route to trifluoromethyl-substituted carbo- and heterocycles)
