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Metallation reactions. XXXVI. A study on the metallation of (methylthio)‐ and (methylsulfonyl)thiophenes
Author(s) -
Fattuoni Claudia,
Usai Michele,
Cabiddu Maria G.,
Cadoni Enzo,
De Montis Stefania,
Sotgiu Francesca,
Cabiddu Salvatore
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440316
Subject(s) - superbase , chemistry , thiophene , sulfur , sulfonyl , organic chemistry , medicinal chemistry , computational chemistry , catalysis , alkyl
Methylthio‐ and methylsulfonyl thiophenes were polymetallated by n ‐buthyllithium and superbase (LICKOR) in one‐step. 2 ‐(Methylthio)thiophene was bimetallated in 5 and in alpha to the methylthio sulfur atom by superbase. 3‐(Methylthio)thiophene was bimetallated in both 2 and 5 positions by the organolithium and trimetallated in these two positions and in alpha to the thioethereal sulfur atom by superbase. 3‐(Methylsulfonyl)thiophene was bimetallated in 2 and in alpha to the sulfonyl sulfur atom by the organolithium while the 2 ‐(methylsulfonyl)thiophene underwent degradation in the same conditions.