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Thermolytic decomposition of benzylic dialkoxy disulfides

โœ Scribed by DiAndra M. Rudzinski; Mary P. McCourt; Ronny Priefer

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
445 KB
Volume
50
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Dialkoxy disulfides have been used as an alkoxy radical source under photolytic conditions. In addition, this class of disulfide thermally decomposes to deliver S 2 to dienes. We examined benzylic dialkoxy disulfides (X-Ph-CH 2 -O-S-S-O-CH 2 -Ph-X) under thermolytic conditions and observed that the rates of decomposition are related to Swain and Lupton's field constant, F. In addition, the observed non 1:1 ratio of alcohol to aldehyde reaffirms Harpp's-postulated cage mechanism. We have shown that the ratio is dependant upon the substituent present which can enhance the pi-stacking ability with the solvent, and thus favor diffusion out of the solvation cage yielding the non 1:1 ratio observed.

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