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30.3.3.1.4.4 Variation 4: Catalyzed by Bromo(dimethyl)sulfonium Bromide

DOI: 10.1055/sos-SD-030-00185

Leung, M.-k.; Luh, T.-Y.Science of Synthesis, (200730277.

Bromo(dimethyl)sulfonium bromide can be used to catalyze the formation of 1,3-dithiolanes 108 from carbonyl compounds 107 (Scheme 55).[‌237‌] In addition, diones such as cyclohexane-1,4-dione and tetrahydropentalene-2,5(1H,3H)-dione are successfully converted into bis(1,3-dithiolanes). Presumably hydrogen bromide, formed in situ from the reaction of ethane-1,2-dithiol with bromo(dimethyl)sulfonium bromide, is responsible for the catalytic behavior. The pH of the mixture drops to about 23 during the course of the reaction.

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