Tetrahedron p. 4583 - 4591 (1969)
Update date:2022-08-02
Topics:
Neale
Bain
Rawlings
2,2′-, 2,4′- and 4,4′-Monothiobisphenol separately rearrange in phenol at 180° in the presence of sodium hydroxide to give similar mixtures containing only 2,2′-, 2,4′- and 4,4′-monothiobisphenol in the approximate ratio, 45:45:10. The rearrangements appear to be intermolecular and they are interpreted in terms of polar processes which lead initially to the formation of o- and p-monothiobenzoquinones. 2,2′-Dithiobisphenol, 4,4′-dithiobisphenol and 4,4′-trithiobisphenol under similar conditions are desulphurated with the evolution of hydrogen sulphide also to give mixtures containing only 2,2 - 2,4′- and 4,4′-monothiobisphenol whilst 3,3′-dithiobisphenol is stable in alkaline phenol even after long periods at 180°. Similar initial heterolyses to o- and p-monothiobenzoquinones are suggested as sources of the monothiobisphenols and displacements of sulphide- or hydrosulphide-ions from intermediate benzeneperthiolate ions by carbanions derived from phenol are suggested as sources of the hydrogen sulphide.
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