Rearrangement reaction with thiobenzophenone

This procedure is adapted from the method of Schlenk and Bergmann.3 Tetraphenylethylene has been prepared by the reaction of diphenylmethane with diphenyldichloromethane 4 by the reaction of diphenyldichloromethane with silver or zinc 4 by the reaction of thiobenzophenone with copper 6 by the reaction of diphenylmethane with sulfur 6 by the reduction of benzophenone with amalgamated zinc in the presence of hydrochloric acid 7 and by the rearrangement of 1,2,2,2-tetraphenylethanol with acetyl chloride.8... 

The applicability of thioketones in the synthesis of heterocyclic compounds has been further demonstrated. The Diels-Alder reaction of thiobenzophenone with l,3>5-cycloheptatriene gave the (2 + 4) cycloadduct (101) in 40% yield. Cycloheptatrienethione (92) yielded the (8 + 2) cycloadduct (102) quantitatively by reaction with maleic anhydride, and the bicyclic compound (103) in 65% yield by reaction with dimethyl acetylenedicarboxylate. Compound (103) was considered to be a rearrangement product of the probably primarily formed (8 + 2) cycloadduct intermediate (104). " The in situ addition of nitrile oxides to aromatic thioketones resulted in formation of 1,4,2-oxathiazoles, " whereas 1,4,2-oxathiazolidines were the products in the reactions of some alicyclic thiones with nitrones. The formation of thio-ozonides (1,2,4-trithiolans) by treatment of thioketones with amines or chloramine T was investigated recently. ... 

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