Further Reactions of Thiols

Further Reactions of Thiols.— Treatment of PhCH2SLi with Bu Li at - 5 C gives the species (PhCH—S )2Li+, which is equally well named the thiobenz-aldehyde dianion or the dianion of the thiol. The carbanion centre is involved in the reaction of the dianion with electrophiles e.g. benzaldehyde gives PhCH(SH)CH(OH)Ph. 

2-Anionic rearrangement from sulphur to carbon under the influence of Bu Li is observed with benzylthiotrimethylsilane, PhCHaSSiMea PhCH(SH)SiMe3.  

A form of anchimeric assistance is involved in the elimination of HCl from 3-chlorobutanethiols (10). Two papers deal with differently based 

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