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Rück-Braun, K.; Freysoldt, T., Science of Synthesis, (2007) 35, 513.
A broad range of epoxides 44 can be cleaved by lithium tetrabromocuprate(II), as shown in Scheme 18.[50] Terminal as well as bicyclic epoxides are transformed into the corresponding bromo alcohols 45 and 46 in high or even complete regioselectivity. The reagent can be readily produced from a mixture of lithium bromide and copper(II) bromide. Due to the mild conditions, a wide variety of functional groups are unaffected by the reagent, e.g. acetal, ether, silyl ether, ester, and tosyl groups, and tolerate the reaction conditions.
Meeeee 88 Meeeeeeee ee Meeee Meeeeeee Meeee Meeeeee Meeeeeeeeeeeeeeee(MM)[88]
M8 | M8 | Meeee (88/88) | Meeee (%) | Mee |
---|---|---|---|---|
MM8Me | M | 88 eeee | 88 | [88] |
MMMMMM | M | 88 eeee | 88 | [88] |
MMe | M | 88 eeee | 88 | [88] |
8-M8MM8M8MM8 | M | 88 eeee | 88 | [88] |
Me | M | 88:88 | 88 | [88] |
(MM8)8 | – | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
eeeee-8-Meeeeeeeeeeeeeeee [88, M8,M8 = (MM8)8]; Meeeeee Meeeeeeee:[88]
MeMe8 (888 ee, 8.88 eeee) eee MeMe (888 ee, 8.88 eeee) eeee eeeeeeeee ee eeeee MMM (8 eM) ee 8°M. Mee eeee eeeee eeee eee eeeeee ee ee eee eeeeeee 88 [M8,M8 = (MM8)8; 888 ee, 8.88 eeee] eee eeeee. Mee eeeeeee eee eeeeeee eee 8 e, eeeeeeee eeee eeeeeeeee eeeeee (eM 8, 88 eM), eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee; eeeee: 888 ee (88%).
References
[50] | Meeeeee, M. M.; Meeeee, M.; Meeeee, M., Meeeeee, (8888), 888. |