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. Author manuscript; available in PMC: 2013 Jul 25.
Published in final edited form as: Org Biomol Chem. 2012 Feb 20;10(16):3164–3167. doi: 10.1039/c2ob07031f

Table 3.

Synthesis of EWG-substituted α-fluoroolefinsa

graphic file with name nihms372986u3.jpg
Entry Product: EWG = Methodb (Solvent) Yieldc (%)
1 graphic file with name nihms372986t8.jpg B (CH2Cl2) 75
2 B (THF) 39d
3 graphic file with name nihms372986t9.jpg B (CH2Cl2) 64
4 graphic file with name nihms372986t10.jpg A (CH2Cl2) 54
5 B (CH2Cl2) 66
6 graphic file with name nihms372986t11.jpg B (CH2Cl2) 68
7 graphic file with name nihms372986t12.jpg B (CH2Cl2) 89
8e graphic file with name nihms372986t8.jpg A (CH2Cl2) 89
9e B (CH2Cl2) 76
a

Sulfone 5a-e: 1 molar equiv; paraformaldehyde: 10 molar equiv.

b

Method A: DBU (3 molar equiv); Method B: Cs2CO3 (2 molar equiv).

c

Yield of isolated, purified product.

d

Other unidentified products were formed.

e

Reaction was performed with Horner-Wadsworth-Emmons reagent Ph-SO2-CH(F)-P(O)(OEt)2.