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. Author manuscript; available in PMC: 2015 Dec 10.
Published in final edited form as: Nat Chem. 2015 Jan 12;7(2):146–152. doi: 10.1038/nchem.2141

Table 1.

Reaction Development with Cyclohexene

graphic file with name nihms742354u1.jpg
entry Cl− source (equiv) oxidant Me3SiCl equiv solvent NMR yield (%) a
6 7 8 9 10
1 n-Bu4NCl (3.0) 11 0.0 MeCN-d3 50 19 3 9 0
2 n-Bu4NCl (3.0) 11 1.0 MeCN-d3 12 61 10 10 0
3 n-Bu4NCl (3.0) 11 2.0 MeCN-d3 0 81 10 0 0
4 n-Bu4NCl (3.0) 11 3.0 MeCN-d3 0 81 8 0 0
5 n-Bu4NCl (2.5) 11 2.0 MeCN-d3 0 74 10 0 0
6b n-Bu4NCl (0.0) 11 2.0 MeCN-d3 54 0 2 0 8
7 n-Bu4NCl (3.0) 11 2.0 CD2Cl2 0 73 12 4 0
8 n-Bu4NCl (3.0) 11 2.0 THF-d8 55 17 2 0 0
9 n-Bu4NCl (3.0) 12 2.0 MeCN-d3 0 71 10 0 0
10 BnEt3NCl (3.0) 11 2.0 MeCN-d3 0 83 10 0 0
a

Measured by 1H NMR spectroscopy with 1,1,2,2-tetrachloroethane (1.0 equiv) as an internal standard.

b

11% of an unidentified species was also observed by 1H NMR spectroscopy.