THERMOLYSIS AND PHOTOLYSIS OF SOME THIOETHERS

Thermolysis of alpha-naphthyl benzyl sulphide (I) in air at 250-degree s-C gives H2S, SO2, benzaldehyde, bibenzyl, stilbene, thio-alpha-napht hol, alpha,alpha'-binapthyl, naphthalene, alpha,alpha'-binapthyl sulph ide, 1-benzyl napthalene, and 2,3,4,5-tetraphenylthiophene. Similar re sults were obtained on heating p-tolyl benzyl sulphide(II) under the s ame conditions in addition to thio p-cresol, p-bitolyl, p-bitolyl-sulp hide, toluene, and phenyl-p-tolyl methane. Thermolysis of I and II in presence of isoquinoline affords in addition to the above products, 1- benzyl isoquinoline. Photolysis of I and II in acetonitrile gives simi lar products to those from thermolysis. A free radical mechanism invol ving homolysis at different sites was postulated to account for the fo rmation of such products.