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. 2015 Feb 13;11:242–248. doi: 10.3762/bjoc.11.27

Table 2.

Synthesis of halohydrins by the reaction of 1-X with alkenes followed by the treatment with NaOH.a

graphic file with name Beilstein_J_Org_Chem-11-242-i002.jpg

Entry Alkene Product Yield (%)b

1 Inline graphic
2a
Inline graphic
5a-Br, 5a-I
5a-Br: 87
2 5a-I: 84c
3 Inline graphic
2b
(Z:E = 72:28)
Inline graphic
5b-Br, 5b-I
5b-Br: 74
(trans:cis = 79:21)
4 5b-I: 94
(trans:cis = 71:29)
5 Inline graphic
2c
Inline graphic
5c-Br, 5c-I
5c-Br: 57
6 5c-I: 53
7 Inline graphic
(E)-2d
Inline graphic
5d-Br, 5d-I
5d-Br: 73
8 5d-I: 35
9 Inline graphic
(Z)-2d
Inline graphic
5d’-Br, 5d’-I
5d’-Br: 75
10 5d’-I: 51

aThe electrolysis of Bu4NBr and Bu4NI was carried out using 1.3 equiv of Bu4NX (based on the alkene which was added after the electrolysis) with 2.1 F/mol of electricity based on Bu4NX. bIsolated yield. cYield was determined by GC.