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. Author manuscript; available in PMC: 2011 Jun 1.
Published in final edited form as: Tetrahedron. 2010 Jun;66(26):4760–4768. doi: 10.1016/j.tet.2010.03.044

Table 4.

Effects of various aldehyde substrates on the vinylogous Wittig transformationa

graphic file with name nihms-196262-f0010.jpg
Entry Ar Product Yieldb [%] E/Z ratioc
1 4-NCC6H4 4a 63 5:2
2 3-NCC6H4 4b 65 5:2
3 2-NCC6H4 4c 60 5:1
4 4-O2NC6H4 4d 51 4:1
5 3-O2NC6H4 4e 57 2:1
6 2-O2NC6H4 4f 50 7:2
7 3-FC6H4 4g 49 5:2
a

Allenic ester in CH3CN (5 mL) was added in one portion to the mixture of the other components in CH3CN (10 mL).

b

Isolated yield.

c

Relating to the geometry around the newly formed double bond; the ratio was determined after integration of the signals of protons Ha and Hb in the 1H NMR spectrum of the crude reaction product.