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Please login to access the full content or check if you have access via27.6.1.6.2 Variation 2: By Reaction of 1,1-Dihalides with Potassium O-Ethyl Dithiocarbonate
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Dabdoub, M. J., Science of Synthesis, (2004) 27, 234.
The treatment of tetrasubstituted geminal dibromides with 2 equivalents of potassium O-ethyl dithiocarbonate results in transient thioketones,[108,110] which are trapped in situ by the reaction with dienes, affording the corresponding Diels–Alder adducts (Scheme 21). This reaction requires 2 equivalents of potassium O-ethyl dithiocarbonate because the mechanism is likely to involve substitution of a bromide by O-ethyl dithiocarbonate, followed by the elimination of the bromide and dithiocarbonate groups, promoted by a second equivalent of dithiocarbonate, to afford the desired thioketone.
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References
[108] | Meeeeeeee, M.; Meeeeeeee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[110] | Meeeeee, M.; Meeeeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.