REGIOCHEMICAL EFFECTS ASSOCIATED WITH NUCLEOPHILIC AROMATIC SUBSTITUTIONS BY BIDENTATE SULFUR NUCLEOPHILES

Aromatic nucleophic substitutions using 2,2-bis(methylthio)ethene 1,1-dithiolate 1 have been investigated. A possible control of the regiochemistry of the compounds resulting from the multiple substitution reactions by this ambident nucleophile have been examined. Starting from hexafluorobenzene, 2a, containing two para fluorines, is obtained. When 2,3,4-trichloro-l,5-dinitrobenzene is reacted with 1, leading to 8, the observed regiochemistry of the two bidentate entering groups is completely modified. The regiochemical aspects of these processes are discussed. © 1990, American Chemical Society. All rights reserved.