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Leung, M.-k.; Luh, T.-Y., Science of Synthesis, (2007) 30, 277.
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 2–3 during the course of the reaction.
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M8 | M8 | Meeee (%) | Mee |
---|---|---|---|
M | (MM8)8Me | 88 | [888] |
M | Me | 88 | [888] |
M | (MM8)8MMMMMM | 88 | [888] |
M | 8-MeMM8M8 | 88 | [888] |
M | 8-eeeeeeeeeee | 88 | [888] |
Me | Me | 88 | [888] |
Me | Me | 88 | [888] |
Me | (MM8)8Me | 88 | [888] |
(MM8)8 | 88 | [888] | |
(MM8)8 | 88 | [888] | |
(MM8)88 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeee(eeeeeeee)eeeeeeeee Meeeeee:[888]
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References
[237] | Meee, M. M.; Meeeee, M.; Meeee, M.; Meeee, M., Mee. M. Mee. Meee., (8888), 8888. |