Comparison of the photooxidation of 1,5-dithiacyclooctane, 1,4-diithiane, and pentamethylene sulfide: another example of remote participation during photooxidation at sulfur ?

The ability of heteroatoms to participate during photooxidations at sulfur is studied by comparing the photooxidation of 1,5-dithiacyclooctane (1,5-DTCO) with those of 1,4-dithiane and pentamethylene sulfide. The photooxidation of 1,5-DTCO differs from those of 1,4-dithiane and pentamethylene sulfide in terms of the large ratio of chemical quenching to total quenching of singlet oxygen, of the nonproduction of sulfone and the large value for the rate constant. It is speculated that these results are due to a new sulfur-sulfur interaction during photooxidation.