Monosubstitution versus disubstitution in the SRN1 reaction of dihalobenzenes with sulfanions. The role of the monosubstitution product and of its anion radical

…, R Beugelmans, M Bois-Choussy…

Index: Amatore, C.; Beugelmans, R.; Bois-Choussy, M.; Combellas, C.; Thiebault, A. Journal of Organic Chemistry, 1989 , vol. 54, # 24 p. 5688 - 5695

Full Text: HTML

Citation Number: 15

Abstract

The competition between mono-and disubstitution of dihalobenzenes by a series of aromatic sulfanions, via the SRNl reaction, is shown to involve two radical chains. The first one, recognized in the earliest works, involves one branching point at the level of the monosubstituted product anion radical. Reoxidation of the latter via electron transfer to the parent dihalide affords the monosubstituted product. Conversely, the route to the ...