Vinyl and allylic nitroalkenes have been converted into the corresponding carbonyl compounds in good yield using tin(II) chloride dihydrate under microwave irradiation.
(a) BarrettA.G.M., and GraboskiG.G., Chem. Rev., 1986, 86, 751; (b) T. Keumi, T. Inagaki, N. Nakayama, T. Morita and H. Kitajama, J. Chem. Soc. Chem. Commun., 1987, 1091; (c) G.W. Kabalka, L.H.M. Guindi and R.S. Varma, Tetrahedron, 1990, 43, 7443 and references cited herein.
2.
(a) NolandW.E., Chem. Rev., 1955, 55, 137; (b) A.H. Pagano and H. Schechter, J. Org. Chem., 1970, 35, 295; (c) M.S. Mourad, R.S. Verma and G.W. Kabalka, Synthesis, 1985, 654; (d) R.S. Varma, M. Varma and G.W. Kabalka, Tetrahedron Lett., 1985, 26, 6013; (e) T. Shono, H. Hamaguchi, H. Mikami, H. Nogusa and S. Kashimura, J. Org. Chem., 1983, 48, 2103; (f) R. Ballini and G. Bosica, Synthesis, 1994, 723.
3.
(a) BartonD.H.R., MotherwellW.B., and ZardS.Z., Tetrahedron Lett., 1983, 24, 5227; (b) R. Tamura, M. Sato and D. Oda, J. Org. Chem., 1986, 51, 4368; (c) N.B. Das, J.C. Sarma, R.P. Sharma and M. Bordoloi, Tetrahedron Lett., 1993, 34, 869.
4.
(a) CaddickS., Tetrahedron, 1995, 51, 10403; (b) S.A. Galema, Chem. Soc. Rev., 1997, 26, 233; (c) A. Loupy and L. Perreux, Tetrahedron, 2001, 57, 9199; (d) P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225; (e) N.B. Das, A. Nayak and B. Nanda, J. Chem. Res., 2004, 712.
5.
Compounds (2a–d) have been compared with the authentic samples prepared from the corresponding 6-nitro cholest-5-ene see: (a) ShoppeeC.W., JenkinsR.H., and SummersG.H.R.J. Chem. Soc., 1958, 1657; (b) C.W. Shoppee and G.H.R. Summers J. Chem. Soc., 1952, 1786; (c) C.W. Shoppee and G.H.R. Summers J. Chem. Soc., 1790; (d) Windaus, Ber., 1920, 53, 490; (e) Byron Riegel and R.M. Dodson, J. Org. Chem., 1948, 13, 424.
6.
Compounds (3a–d) have been compared with the authentic samples prepared see: YateP., and StiverS., Can. J. Chem., 1987, 65, 2203.
7.
Phenyl acetone (5) has been compared with the authentic sample prepared from 2-nitro-1-phenylpropene see: MouradM.S., VarmaR.S., and KabalkaG.W., Synthesis, 1985, 654.
8.
AizpuruaJ.M., OiarbideM., and PalomaC., Tetrahedron Lett., 1987, 28, 5365.
