SOME OBSERVATIONS OF REACTIONS BETWEEN PHENOL AND SULPHUR

Preliminary investigations of the reactions between phenol and sulphur in the presence of NaOH at 140° and at 180° are reported. With the ratio PhOH:S ≥ 5:1, the products are mixtures of 2,2′-, 2,4′- and 4,4′-monothiobisphenols and 50% of the incident sulphur is eliminated as hydrogen sulphide. NMR spectra in the presence of hexamethylphosphoramide have demonstrated the intermediate formation of polythobisphenols at 140° and it is suggested that a sequence which involves desulphurations of these polythiobisphenols in a manner similar to that suggested in the previous paper for 4,4′-trithiobisphenol may be involved. With the ratio PhOH: S = 1: > - 1, 50% of the incident sulphur again is eliminated as hydrogen sulphide and in the limit the products appear to be monosulphidically bridged oligonuclear phenols which may be formed by a similar sequence of reactions. © 1969.