The reactions of vinyl(phenyl)iodonium salts with sodium selenide, sodium sulfide, sodium azide and potassium thiocyanate have been studied. Divinylic selenides, divinylic sulfides, vinylic azides and vinylic thiocyanates were synthesised stereoselectively in good yields.
(a) VarvoglisA., Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997; A. Varvoglis, Tetrahedron, 1997, 53, 1179; (b) P.J. Stang and V.V. Zhdankin, Chem. Rev., 1996, 96, 1123; (c) V.V. Zhdankin and P.J. Stang, Chem. Rev., 2002, 102, 2523; (d) T. Wirth and U.H. Hirt, Synthesis, 1999, 1271; (e) A. Kirschning, Eur. J. Org. Chem., 1998, 11, 2267; (f) T. Kitamura and Y. Fujiwara, Org. Prep. Proced. Int. 1997, 29, 409; (g) R.M. Moriarty and O. Prakasa, Org. React., 1999, 54, 273; (h) M. Ochiai, In Chemistry of Hypervalent Compounds; AkibeK., ed.; VCH Publishers: New York, 1999; Chapter 13, pp 359-387; M. Ochiai, J. Organomet. Chem., 2000, 611, 494; (i) T. Okuyama, Acct. Chem. Res., 2000, 35, 12; (j) V.V. Zhdankin and P.J. Stang, Tetrahedron, 1998, 54, 10927; (k) V.V. Grushin, Chem. Soc. Rev., 2000, 29, 315.
2.
(a) OchiaiM., SumiK., TakaokaY., KurishimaM., NagaoY., ShiroM., and FujitaE., Tetrahedron, 1988, 44, 4095; (b) M. Ochiai, K. Oshima and Y. Masiki, Tetrahedron Lett., 1991, 52, 7711; (c) T. Okuyama, T. Takino, T. Sueda and M. Ochiai, J. Am. Chem. Soc., 1995, 117, 3360.
3.
(a) YanJ., and ChenZ.C., Synth. Commun., 2000, 30, 1009; (b) J. Yan and Z.C. Chen, Synth. Commun., 2000, 30, 2359.
