Metallation reactions. Part 35: A change of the regiochemistry in the metallation of (alkylthio)arenes

CABIDDU, MARIA GRAZIA;Cabiddu S;CADONI, ENZO;De Montis S;FATTUONI, CLAUDIA;Melis S.

2004-01-01

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Abstract

The metallation reaction of bromo(alkylthio)benzenes is described. The results show the complementarity of these reactions with the metal–hydrogen exchange reaction. In fact, monometallation of bromo(methylthio)benzenes afforded products substituted in para or meta or ortho to the thioethereal function while bimetallation led to aS,para, aS,meta and aS,ortho disubstituted products. Analogously, the monometallation of 4-bromo-(isopropylthio)benzene afforded para-monosubstituted and ortho,para-disubstituted products.