Dibenzyl disulfide, cleavage

Cleavage of Dibenzyl Disulfide with Lithium Aluminum Hydride... 

The photochemistry of dibenzyl sulfoxide 10 was briefly reported in the mid 1960s [21,22]. It was said to decompose mainly to benzyl mercaptan (isolated as the disulfide 17) and benzaidehyde 16. Though no mechanism was suggested at the time, it is now clear that these products arise from a standard a-cleavage mechanism, followed by secondary photolysis of the sulfenic ester 13. The careful reader will note that the yield of bibenzyl (19) is very low in comparison to photolysis of dibenzyl ketone. Sulfinyl radicals rarely lose SO, though some net extrusions are discussed later. 

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