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Hartung, J., Science of Synthesis, (2007) 35, 290.
tert-Butyl hypobromite is a reddish orange liquid that is stable for long periods in the cold and dark. It can be distilled under reduced pressure (bp 44–45°C/85 Torr), but decomposes rapidly at about 85°C.[12,13] If photolyzed in the presence of linear or cyclic alkanes, it is able to convert hydrocarbons into bromoalkanes. In situ generated tert-butyl hypobromite, on the other hand, is applicable in aliphatic bromination without external photoactivation, e.g. to give 2 (Scheme 5).[13] The relative primary/secondary/tertiary C—H reactivity ratio of hydrocarbons toward the reagent is consistent with the assumption that the electrophilic tert-butoxyl radical and not the less reactive Br• acts as major hydrogen-atom abstractor.
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Meeeee | Meeeeeeeeee Meeeeee | Meeee (%) | Mee |
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Meeeeeeeeeeeeeee (8, M8 = Me); Meeeeee Meeeeeeee:[88]
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References
[12] | Meeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[13] | Meeeeee, M.; Meeee, M., Meeeeeeee, (8888), 8888. |