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1‐(Alkylsulfinyl‐ and ‐alkylsulfonyl)‐2‐(F‐alkyl)ethynes − Applications in Cycloaddition Reactions and Synthesis of Aromatic Derivatives
Author(s) -
Bouillon JeanPhilippe,
Musyanovich Rostyslav,
Portella Charles,
Shermolovich Yuriy
Publication year - 2001
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(200110)2001:19<3625::aid-ejoc3625>3.0.co;2-n
Subject(s) - chemistry , cycloaddition , alkyl , deprotonation , alkylation , adduct , medicinal chemistry , organic chemistry , catalysis , ion
Syntheses and cycloaddition reactions of 1‐(alkylsulfinyl‐ and ‐alkylsulfonyl)‐2‐(F‐alkyl)ethynes are described. These alkynes are strong dienophiles and produce the corresponding F‐alkylated sulfinyl‐ and sulfonylbenzenes in two high‐yielding steps. When treated under basic conditions, the (F‐alkyl)cyclohexadienyl adducts were converted into a mixture of the same aromatic compounds and the corresponding α‐defluorinated derivatives, by way of a competitive oxidation/(HF) elimination on the deprotonated intermediates.