Organofluorine compounds. Part XIII. The halide-promoted fragmentation of 1-chloro-1-fluoro-2-(a-silylaklyl)cyclopropanes: a new entry to fluorodienes

When heated in the presence of Bu4N+.X- (X = F, Cl), 1-chloro-1-fluoro-2-(trimethylsilyl)methylcyclopropanes I (R = H, Me; R1 = Me, Et) undergo smooth ring-opening fragmentation to give 2-fluorobutadienes RCH:CFCR1:CH2 with high yields. Despite unfavorable geometries, the reaction is concerted and the inversion mode of rotation dominates over the retention mode by a factor of roughly 100. [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 67, 1, 284-8
Year:
1984
Keywords:
Note:
CAN 101:23566
29-6
Organometallic and Organometalloidal Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in English.
90682-39-6 Role: RCT (Reactant), RACT (Reactant or reagent) (cyclopropanation of); 338-68-1P; 52021-25-7P; 90682-41-0P; 90682-42-1P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in ring opening of silylmethylcyclopropane); 18292-38-1P; 54081-41-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cyclopropanation of); 90682-36-3P; 90682-37-4P; 90682-38-5P; 90682-40-9P; 90760-84-2P; 90760-85-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ring opening of, mechanism of); 115-11-7; 513-35-9 Role: RCT (Reactant), RACT (Reactant or reagent) (silylation of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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