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35.2.1.1.1.2 Method 2: Reaction with tert-Butyl Hypobromite

DOI: 10.1055/sos-SD-035-00260

Hartung, J.Science of Synthesis, (200735290.

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 4445°C/85Torr), 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 CH 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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