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.
Metallation Reactions. XXXVI. A Study on the Metallation of (Methylthio)- and (Methylsulfonyl)thiophenes
FATTUONI, CLAUDIA;CADONI, ENZO;CABIDDU, MARIA GRAZIA
2007-01-01
Abstract
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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