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Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Zając, A.; Mikołajczyk, M., Science of Synthesis, (2008) 39, 52.
Sulfonamides react with alcohols in the presence of acidic catalysts to form the corresponding sulfonates (see reviews in Houben–Weyl, Vol. E 11, p 1093 and elsewhere[8]). Of particular importance are the bis(trifluoromethylsulfonyl)imides that serve as a source of the trifluoromethylsulfonyl unit.[9] For example, 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, the Comins reagent, is a convenient alternative to trifluoromethanesulfonic anhydride and, among others, is used for the synthesis of alkenyl trifluoromethanesulfonates from the enolates of carbonyl compounds. A specific example, uses 3,4-dihydro-2(3H)-thiophenone as the starting material en route to 4,5-dihydro-2-thienyl trifluoromethanesulfonate (108) (Scheme 83).[233–235] N,N-Bis(trifluoromethylsulfonyl)aniline (N-phenyltriflimide) is also effective in similar transformations (Scheme 83).[234,236–238]
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References
| [8] | Meeeee Meee, M. M.; Meeeee, M. M.; Meeeeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee Meeeeeeeeeeeeee, Meeeeeeee, M. M.; Meee-Meee, M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888–888. |
| [9] | Meeeeeeeeeee, M.; Meeeeeeeee, M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee Meeeeeeeeeeeeee MM, Meeeeeeee, M. M.; Meeeee, M. M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, Meeeeee 8.88. |
| [233] | Meee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [234] | M'Meee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Meeeeee, (8888), 888. |
| [235] | Meeeee, M. M.; Meeee, M.-e., M. Me. Meee. Mee., (8888) 888, 88888. |
| [236] | Meeee, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [237] | Meeee, M.; Meee, M.; Meeeeeee, M.; Meeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [238] | Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M. M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 88-8, 8888.
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