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The Halide‐promoted fragmentation of 1‐chloro‐1‐fluoro‐2‐(a‐silylakyl))cyclopropanes: A new entry to fluorodienes
Author(s) -
Schlosser Manfred,
Dahan Rahel,
Cottens Sylvain
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670134
Subject(s) - chemistry , halide , fragmentation (computing) , trimethylsilyl , fluoride , chloride , walden inversion , medicinal chemistry , organic chemistry , inorganic chemistry , computer science , operating system
When heated in the presence of tetrabutylammonium fluoride or chloride, 1‐chloro‐1‐fluoro‐2‐(trimethylsilyl)methyl‐cyclopropanes ( 1 , 2 and 3 ) undergo smooth ring‐opening fragmentation to afford 2‐fluoro‐butadienes (( 4 , 5 and 6 resp.) with high yields. Despite unfavorable geometries, the reaction is concerted and the inversion mode of rotation dominates over the retention mode by a factor roughly 100.