Abstract

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)]

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