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Synthèses de produits organofluorés VI Solvolyse de chlorofluorocyclopropanes
Author(s) -
Bessière Yvonne,
Schlosser Manfred
Publication year - 1976
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.19760590329
Subject(s) - chemistry , solvolysis , allylic rearrangement , carbocation , medicinal chemistry , toluene , acetic acid , alkyl , organic chemistry , hydrolysis , catalysis
Fluoro‐organic Syntheses VI: The Solvolysis of Chlorofluoro‐cyclopropanes 2‐Fluoro‐allylic carbocations, generated from 1‐chloro‐1‐fluoro‐cyclopropanes or 2‐fluoro‐allyl p ‐toluene‐sulfonates in water or acetic acid, undergo either proton loss or addition of hydroxyl or acetoxyl. In the latter case, an alkyl‐substituted 2‐fluoro‐allyl ion leads predominantly to the more branched product ( e.g. 3‐fluoro‐2‐methyl‐3‐buten‐2‐ol) which may be converted into the less branched one ( e.g. 2‐fluoro‐3‐methyl‐2‐buten‐2‐ol) through reversible reactions.