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Entry |
Alkene |
Bromohydrin |
Yield (%)a |
---|---|---|---|
1 |
(Z)-C6H5CH=CHC6H5 |
threo-C6H5CH(OH)CH(Br)C6H5 |
82 |
2 |
(E)-C6H5CH=CHCH3 |
erythro-C6H5CH(OH)CH(Br)CH3 |
92 |
3 |
(Z)-C6H5CH=CHCH3 |
threo-C6H5CH(OH)CH(Br)CH3 |
95 |
4 |
C6H5CH=CH2 |
C6H5CH(OH)CH2Br |
76 |
5 |
C6H5-C(CH3)=CH2 |
C6H5C(CH3)(OH)CH2Br |
89 |
6 |
C6H5CH2CH=CH2 |
C6H5CH2CH(OH)CH2Br |
83 |
7 |
(E)-(CH3)3CCH=CHCH3 |
erythro-(CH3)3CCH(Br)CH(OH)CH3 |
90 |
8 |
(Z)-(CH3)3CCH=CHCH3 |
threo-(CH3)3CCH(Br)CH(OH)CH3 |
90 |
9 |
(CH3)3CCH=CH2 |
(CH3)3CCH(Br)CH2OH |
89 |
10 |
(CH3)3CC(CH3)=CH2 |
(CH3)3CC(CH3)(OH)CH2Br |
60b |
aAverage yield from two or more runs. |
|||
bAccompanied by 24% dibromide. |
Appendix
Compounds Referenced (Chemical Abstracts Registry Number)
petroleum ether
erythro-2-Bromo-1,2-diphenylethanol
Ethanol, 2-bromo-1,2-diphenyl-, erythro-
(Z)-C6H5CH=CHC6H5
threo-C6H5CH(OH)CH(Br)C6H5
(E)-C6H5CH=CHCH3
erythro-C6H5CH(OH)CH(Br)CH3
(Z)-C6H5CH=CHCH3
threo-C6H5CH(OH)CH(Br)CH3
C6H5CH=CH2
C6H5CH(OH)CH2Br
C6H5-C(CH3)=CH2
C6H5C(CH3)(OH)CH2Br
C6H5CH2CH=CH2
C6H5CH2CH(OH)CH2Br
(E)-(CH3)3CCH=CHCH3
erythro-(CH3)3CCH(Br)CH(OH)CH3
(Z)-(CH3)3CCH=CHCH3
threo-(CH3)3CCH(Br)CH(OH)CH3
(CH3)3CCH=CH2
(CH3)3CCH(Br)CH2OH
(CH3)3CC(CH3)=CH2
(CH3)3CC(CH3)(OH)CH2Br
ether, diethyl ether (60-29-7)
sodium chloride (7647-14-5)
hydrogen bromide (10035-10-6)
oxygen (7782-44-7)
nitrogen (7727-37-9)
acetone (67-64-1)
magnesium sulfate (7487-88-9)
N-bromosuccinimide (128-08-5)
hexane (110-54-3)
N-Bromoacetamide (79-15-2)
dimethyl sulfoxide (67-68-5)
bromotrinitromethane (560-95-2)
(E)-stilbene (103-30-0)