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

Table 3.

Synthesis of epoxides by the reaction of 1-X with alkenes followed by the treatment with NaOMe.a

graphic file with name Beilstein_J_Org_Chem-11-242-i013.jpg

Entry Alkene Product X Yield (%)b

1 Inline graphic
2a
Inline graphic
6a
Br 95c
2 I 96c
3 Inline graphic
2b
(Z:E = 72:28)
Inline graphic
6b
Br 68
(cis:trans = 74:26)
4 I 89
(cis:trans = 74:26)
5 Inline graphic
2c
Inline graphic
6c
Br 73c
6 I 86c
7 Inline graphic
(E)-2d
Inline graphic
6d
Br 53
8 I 38d
9 Inline graphic
(Z)-2d
Inline graphic
6d’
Br 60
10 I 67d
11 Inline graphic
2e
Inline graphic
6e
Br 52e
12 I 57e
13 Inline graphic
2f
Inline graphic
6f
Br 49e
14 I 47e
15 Inline graphic
2g
Inline graphic
6g
Br 69
16 I 0

aThe electrolysis was carried out using 1.3 equiv of Bu4NBr or Bu4NI (based on the alkene which was added after electrolysis) with 2.1 F/mol of electricity based on Bu4NBr or Bu4NI. bIsolated yield. cYield was determined by GC. d2.0 Equiv of Bu4NI was used. eReacted with 2.5 equiv of NaOMe for 2 h.