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Braun, M., Science of Synthesis, (2007) 35, 389.
As is the case for the synthesis of saturated bromoalkanes, the replacement of sulfonyloxy groups in alkyl and aryl sulfonates by bromide is a reliable and mild method. Thus, propargylic toluenesulfonates are converted into propargylic bromides by treatment with lithium[24] or sodium bromide,[25] in some cases under phase-transfer catalysis.[26] The more reactive methanesulfonates derived from propargylic alcohols are more frequently applied. Again, this is analogous to the synthesis of alkali bromides[27–30] following the protocols outlined in Section 35.2.1.5
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References
| [11] | Meeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [24] | Meeeeeeeeeee, M. M.; Meeeeeeee, M.; Meeeee, M.; Meeeee, M. M., Me., Mee. M. Meee., (8888) 88, 8888. |
| [25] | Meee-Meeeeeeee, M., MM 88 88 888, (8888); Meee. Meeee., (8888) 888, 888888. |
| [26] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 888, 888888. |
| [27] | Meeeeeeee, M.; Meeeeeeeee, M.; Meeee, M. M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [28] | Meeeee, M. M.; Meeeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [29] | MeeMeeee, M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [30] | Meeeeeeee, M.; Meeeeee, M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [31] | Meeee, M.; Meeeeèee, M.; Meeé, M., Meeeeeeeeee, (8888) 88, 8888. |
| [32] | Meeee, M.; Meeee, M.; Meee, M., Meee. Mee. Meee. Me., (8888), 888. |
| [33] | Meeeeeeee, M. M.; Meeeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [34] | Meeeeee, M.; Meeé, M., Meeee. Meeeee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) 8/8, 888.
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