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García Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J., Science of Synthesis, (2008) 39, 348.
The reactions of organic halides and sulfonates with dimethyl sulfoxide proceed by route B as depicted in Scheme 117 in Section 39.4.2.2, via formation of an alkoxydimethylsulfonium salt by direct nucleophilic displacement of a leaving group by dimethyl sulfoxide. High yields are reported in the oxidation of α-halo esters or acids,[610] phenacyl halides,[566,611] benzyl halides, primary sulfonates,[612,613] primary iodides,[614] a limited number of secondary halides,[615,616] and secondary 4-toluenesulfonates.[617–619]
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M8 | M8 | M | Meeee (%) | Mee |
---|---|---|---|---|
(MM8)8Me | M | Me | 88 | [888] |
(MM8)8MM=MM8 | M | M | 88 | [888] |
(MM8)8M≡MM | M | M | 88 | [888] |
8-MeM8M8 | M | Me | 88 | [888] |
Me | Me | Me | 88 | [888] |
(MM8)8MM | M | M | 88 | [888] |
(M)-(MM8)8MM=MM(MM8)8Me | M | MMe | 88 | [888] |
(M)-(MM8)8MM=MM(MM8)8Me | M | MMe | 88 | [888] |
MM8MMe | MM8MMe | MMe | 88 | [888] |
8-M8MM8M8 | M | MMe | 88 | [888] |
References
[566] | Meeeeeee, M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[610] | Meeeeeeeee, M. M.; Meee, M. M., Meee. Mee. (Meeeee), (8888), 88. |
[611] | Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[612] | Meeeeeee, M.; Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[613] | Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[614] | Meeeeeeee, M., M. Me. Mee Meee. Mee., (8888) 88, 888. |
[615] | Meeeee, M. M.; Meeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[616] | Meeeeeeeee, M. M., Meee. Mee. (Meeeee), (8888), 888. |
[617] | Meeeeee, M. M.; Meeeeeee, M.; Meeeeeee, M., Meee. Mee. Meee. Me., (8888), 888. |
[618] | Meeee, M. M.; Meeee, M. M., M. Meee. Mee., (8888), 8888. |
[619] | Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Mee, M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[620] | Meeeeee, M. M.; Meeeee, M., M. Meee. Mee., (8888), 888. |
[621] | Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.