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. Author manuscript; available in PMC: 2009 Jan 27.
Published in final edited form as: J Org Chem. 2007 Mar 6;72(7):2469–2475. doi: 10.1021/jo062526t

Table 1.

Ratios of syn/anti Isomers at Different Temperatures for Model Compounds 6a-14a. The experiments were performed in CDCl3 unless stated otherwise.

Entry Compound Ar1 Ar2 syn/anti Ratio in CDCl3 at different temp.
−10 −20 −30 −40 −50 (°C)
1 6a C6H4NMe2 C6F5 15.7 17.5 20.7 26.5 28.0
2 6b C6H4NMe2 C6HF4 5.37 6.04 6.61 7.36 8.87
3 6c C6H4NMe2 C6H2F3 1.62 1.70 1.83 1.90 1.93
4 6d C6H4NMe2 C6H3F2 0.72 0.71 0.72 0.72 0.74
5 6e C6H4NMe2 C6H4F 0.54 0.53 0.48 0.47 0.47
6 7a C6H5 C6F5 11.0 11.7 13.7 15.7 18.0
7 7f C6H5 C6H4NO2 2.63 2.78 2.94 3.08 3.27
8 7e C6H5 C6H4F 0.55 0.54 0.53 0.50 0.47
9 7g C6H5 C6H5 0.30 0.29 0.26 0.24 0.21
10 7h C6H5 C6H4Me 0.19 0.17 0.16 0.14 0.12
11 7i C6H5 C6H4OMe 0.23 0.22 0.19 0.18 0.17
12 8a C6H4NO2 C6F5 5.6 6.0 6.8 7.6 8.9
13 8f C6H4NO2 C6H4NO2 2.66 2.73 2.85 2.94 3.05
14 8e C6H4NO2 C6H4F 0.96 0.92 0.90 0.89 0.89
15 8g C6H4NO2 C6H5 0.59 0.56 0.55 0.53 0.50
16 8h C6H4NO2 C6H4Me 0.54 0.51 0.48 0.46 0.44
17 8i C6H4NO2 C6H4OMe 0.61 0.59 0.57 0.54 0.52
18 9a C6H4Me C6F5 13.5 15.2 17.2 18.7 21.3
19 10a C6H4OMe 10.6 12.0 13.1 15.8 18.2
20 11a C6H3Me2 15.2 17.5 19.8 21.0 23.3
21 12a C6H2Me3 17.1 19.1 21.3 23.8 26.1
22 13 C6H4Me CH3 1.99 2.08 2.27 2.40 2.58
23 14 CH3 CH3 0.32 0.32 0.30 0.28 0.27