Metallation reactions. XXXVI. A study on the metallation of (methylthio)‐ and (methylsulfonyl)thiophenes | Zendy

Fattuoni Claudia | Zendy; Usai Michele | Zendy; Cabiddu Maria G. | Zendy; Cadoni Enzo | Zendy; De Montis Stefania | Zendy; Sotgiu Francesca | Zendy; Cabiddu Salvatore | Zendy

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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.

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