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Please login to access the full content or check if you have access via35.2.1.5.2.1 Variation 1: Reaction of Alcohols with Aqueous Hydrobromic Acid
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Braun, M., Science of Synthesis, (2007) 35, 326.
The treatment of alcohols with hydrobromic acid provides a simple access to alkyl bromides 6, and the protocol has been applied to primary, secondary, and tertiary alcohols as well as to diols and amino alcohols (Scheme 6). As far as alcohols with a stereogenic hydroxy-bearing carbon atom have been applied, they have been mostly used as racemates (see Houben–Weyl, Vol. 5/4, pp 374–387). However, the reaction of nonracemic alcohols has been described as well, and the stereochemical outcome in these reactions has been investigated.[16–18]
Meeeee 8 Meeeeeeeeee ee Meeee Meeeeeee eeee Meeeeeee eeee Meeeeee Meeeeeeeeee Meee[88–88]
M8 | Meeee (%) | Mee |
---|---|---|
eMe | 88 | [88] |
8-(8-eeeeeeee)eeeee | 88 | [88,88] |
(MM8)8MM8 | 88–88e | [88] |
(MM8)8MMMe | 88e | [88] |
MMe8(MM8)8MM=MM8 | 88 | [88] |
MM(MM8)8 | 88 | [88] |
e Meeeeee eeeeeeee ee eee eeeeeeeeeeee eeee.
Mee eeeeeeee ee eeeeeee eeeeeee ee eeeeeee eeeeeeeeeee eeee eeeeeeee e eeeeeeee eeeeeee eee eee eeeeeeeeee ee eeeeeeee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee 8 eeeee eeee eeeeeeeeee (Meeeee 8). Meeeeeeeeeeee, eeeeeee eeeeeee ee eeee ee ee eeeeeeee.[88]
Meeeee 8 Meeeeeeeeee ee Meeeeeee Meeee Meeeeeee eeee Meeeeeee eeee Meeeeee Meeeeeeeeee Meee ee eee Meeeeeee ee Meeeeee Meeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-(8-Meeeeeeeee)eeeeeeeeeee [8, M8 = 8-(8-Meeeeeee)eeeee]; Meeeeee Meeeeeeee:[88,88]
M eeee ee 8-(8-eeeeeeee)eeeeeee (888 e, 888 eeee) eee 88% MMe (888 eM) eee eeeeeeee eee 8 e. M eeeeee ee 888 eM eee eeeeeeeee eee. Mee eeeeeee eeeee ee eee eeeeeeeee eeeeeee eee eeeeeeeee eee eeeeeeee eeee eee eeeeeeee eeeeeee, ee eeeee eeeeeee 88-eM eeeeeee ee 88% MMe eee eeeee. Mee eeeeeee eee eeeeeeee eee 8 e eee, eeeeeeeeee, e eeeeee ee 88 eM eee eeeeeeeee eee. Meee, eee eeeeeeee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 888 e (88%); ee 888–888°M/888 Me.
8-Meeee-8,8,8,8,8,8-eeeeeeeeeeeeeeeeee [8, M8 = MM(MM8)8]:[88]
Me 8,8,8,8,8,8-eeeeeeeeeeeeeeeee-8-ee (88.8 e, 888 eeee) eee eeeee 88% MMe (888 eM). Meee, e eeee eeeeeeeeeeee eee eeeeeeeee eeeeeee 88°M (eeeeeee eeeee ee eee eeeeeee) eee 888°M, eeeee eee eeeeee ee eee eeeeee eee eeeeeee ee eee eeee. Me eee eeeeeeeeee, eee eeeeeee eee eeeeeeeee eeee eee eeeeeee eeeee eee eeeee (MeMM8). Meeeeeeeeee ee eee eeeeeee eeeeeeeee eee eeeeeee; eeeee: 88 e (88%); 8M MMM (MMMe8, δ): 8.88 (e, 8M), 8.88 (e, 8M, eeeeeeeee eeee M8M).
eeee-Meeee Meeeeee (8, M8 = M8 = Me); Meeeeee Meeeeeeee:[88]
M eeeeeee ee MeMe (88.88 e, 888 eeee) eee e-MeMM (8.888 e, 888 eeee) eee eeeeeee ee ee Meeeeeeeee eeeee ee 8°M. Me 88% MMe eee eeeee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeeeeeeeeee eee 8 e. Mee eeeee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eeeeeeee eeeeee (8 × 888 eM) ee eeeeee eee MMe eee eee eeeeeeeee e-MeMM, eee eeee eeeee (Me8MM8), eeeeee 88.8% eeee e-MeMe; eeeee: 88.88 e (88%); eeee eee eeeee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeee eeeeeee ee e eeeeeeeee eeeeee; ee 88.8°M.
References
[16] | Meeeee, M. M.; Meeeee, M. M., M. Meee. Meee., (8888) 88, 888. |
[17] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M., M. Meee. Mee., (8888) 8888. |
[18] | Meeee, M. M.; Meeee, M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[19] | Meeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Me., M. Mee. Meee., (8888) 88, 888. |
[20] | Meeeee, M. M., M. Mee. Meee., (8888) 8, 888. |
[21] | Meeeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
[22] | Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[23] | Meeee'ee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[24] | Meeeeeeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[25] | Meeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
[26] | Meeeee, M.; Meeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.