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1,1‐Bis(ethylsulfanyl)perfluorobut‐1‐ene as Starting Material for the Synthesis of Substituted 2‐Trifluoromethylfurans and ‐pyrroles
Author(s) -
Bouillon JeanPhilippe,
Hénin Béatrice,
Huot JeanFrançois,
Portella Charles
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:9<1556::aid-ejoc1556>3.0.co;2-4
Subject(s) - chemistry , nucleophile , amine gas treating , hydrolysis , ene reaction , selectivity , thioester , acetone , organic chemistry , condensation , medicinal chemistry , catalysis , physics , thermodynamics , enzyme
In a two‐step sequence (condensation with acetone enolate/acid hydrolysis), 1,1‐bis(ethylsulfanyl)perfluorobut‐1‐ene was converted into the corresponding S ‐ethyl 4‐oxo‐2‐pentafluoroethylpentanethioate. This thioester proved to be a versatile intermediate, leading, in the presence of aliphatic amine, to substituted 2‐trifluoromethylfurans and/or ‐pyrroles. The selectivity of these heterocyclisations depends on the reaction conditions and on the basicity/nucleophilicity balance of the amine. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)