Fluorinated benzaldehydes undergo solventless Wittig olefination with stabilised phosphoranes. Even with less reactive, stabilised phosphoranes, such as acetylmethylidenetriphenylphosphorane, the reactions have been found to be exothermic.
TanakaK., and TodaF., Chem. Rev., 2000, 100, 1025.
2.
ThiemannT., WatanabeM., TanakaY., and MatakaS., New J. Chem., 2004, 28, 578.
3.
(a) LiuW., XuQ., MaY., LiangY., DongN., and GuanD., J. Organomet. Chem., 2001, 625, 128; (b) C. Xu, G. Chen, C. Fu and X. Huang, Synth. Commun., 1995, 25, 2229; (c) C. Xu, G. Chen and X. Huang, Org. Prep. Proced. Int., 1995, 27, 559.
4.
SpinellaA., FortunatiT., and SorienteA., Synlett, 1997, 93.
5.
BalemaV.P., WienchJ.W., PruskiM., and PecharskyV.K., J. Am. Chem. Soc., 2002, 124, 6244.
6.
ThiemannT., TanakaY., IdetaK., and MatakaS., Centr. Eur. J. Chem., 2006, 4, 403.
7.
for typical examples, see: (a) CoreyE.J., ClarkD.A., GotoG., MarfatA., MioskowskiC., SamuelssonB., and HammerströmS., J. Am. Chem. Soc., 1980, 102, 1436 (for DME); (b) S. Fliszàr, R.F. Hudson and G. Salvadori, Helv. Chim. Acta, 1964, 47, 159 (for chloroform); (c) D. Spitzner and H. Swoboda, Tetrahedron Lett., 1986, 27, 1281 (for benzene); (d) T. Thiemann, D. Ohira, Y.Q. Li, T. Sawada, S. Mataka, K. Rauch, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Perkin Trans. 1, 2000, 2968 (for benzene); (e) J.-P. Surivet, J.-N. Volle and J.M. Vatèle, Tetrahedron: Asymmetry, 1996, 7, 3305 (for toluene); (f) J. Vicente, M.T. Chicote, J. Fernandes-Baeza and A. Fernandez-Baeza, New J. Chem., 1994, 18, 263 (for dichloromethane).
Koszytkowka-StawinskaM., and SasW., J. Chem. Res., 1999, (S), 694; (M) 2945.
13.
WatanabeM., Ribeiro MoraisG., MatakaS., IdetaK., and ThiemannT., Z. Naturforsch.2005, 60B, 909.
14.
(a) RamirezF., and DershowitzS., J. Org. Chem., 1957, 22, 41; (b) W.J. Considine, J. Org. Chem., 1962, 64, 7; (c) N.F. Osborne, J. Chem. Soc., Perkin Trans. 1, 1982, 1429; (d) M.I. Shevchuk, V.L. Mikailu, V.I. Laba and A.V. Sviridova, Zh. Obshch. Khim., 1986, 56, 347; (e) M.M. Kayser, J. Zhu, and D.L. Hooper, Can. J. Chem., 1997, 75, 1515; (f) S. Trippett and D.M. Walker, J. Chem. Soc., 1959, 3874; (g) M. Mauduit, C. Kouklovsky and Y. Langlois, Tetrahedron Lett., 1998, 39, 6857; (h) E. Hedaya and S. Theodoropoulos, Tetrahedron, 1968, 24, 2241.
15.
SurivetJ.-P., HubschwerlenC., and Zumbrunn AcklinC. (Actelion Percurex AG, Switz.), PCT Int. Appl. WO 2006038172 (Apr. 13, 2006); Chem. Abstr., 2006, 144, 390745; C. Hubschwerlen, J.-P. Surivet, C. Zumbrunn Acklin (Actelion Percurex AG, Switz.), PCT Int. Appl. WO 2006032466 (March 30, 2006); Chem. Abstr., 2006, 144, 350718.
16.
StrohmeierG.A., and KappeC.O., J. Comb. Chem., 2002, 4, 154.
17.
RossR.Jr., NguyenD.V., SzapacsE.M., SmithD.F., and ShaberS.H. (Dow Agrosãences LLC, USA), US 6348627 (Feb. 9, 2002); Chem. Abs., 2002, 136, 183604.
18.
ChatterjeeA.K., ChoiT.-L., SandersD., and GrubbsR.H., J. Am. Chem. Soc., 2003, 125, 11360.
19.
(a) YiC., and HuaR., Tetrahedron Lett., 2006, 47, 2573; (b) H.U. Blaser and A. Spencer, J. Organomet. Chem., 1982, 233, 267.
20.
IkemotoT., FukuyoS., and YasuokaJ. (Sumitomo Chemical Company, Ltd., Japan), PCT Int. Appl. WO 2006123762 (Nov. 23, 2006); Chem. Abs., 2006, 145, 505327.
21.
RendyR., ZhangY., McElreaA., GomezA., and KlumppD.A., J. Org. Chem., 2004, 69, 2340.
22.
JeschkeP., LindnerW., Wachendorff-NeumannU., and ErdelenC. (Bayer A.-G., Germany), DE 4124151 (Jan. 21, 1993); Chem. Abs., 1993, 118, 213088.
