A.V. Martynov et al. / Journal of Organometallic Chemistry 674 (2003) 101Á
/
103
103
[2] A. Ogawa, H. Kuniyasu, M. Takeba, T. Ikeda, N. Sonoda, T.
Hirao, J. Organometal. Chem. 564 (1998) 881 (references cited
therein).
3.2. The NiCl2(dppp)-catalyzed cross-coupling of (Z)-
1,2-bis(ethylseleno)ethene (1) with n-butyl magnesium
bromide (2b)
[3] R.J.P. Corriu, J.P. Masse, J. Chem. Soc. Chem. Commun. (1972)
144.
Analogously to the procedure described for 2c, the
ethene 1 (484 mg, 2 mM), NiCl2(dppp) (111 mg, 0.2
mM), and 8.4 ml of the 0.95 N ether solution of butyl
magnesium bromide (2b) (8 mM) were reacted. The
residue after the evaporation in vacuo contains accord-
[4] K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S.
Kodama, I. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc.
Jpn. 49 (1976) 1958.
[5] E. Wenkert, T.W. Ferreira, E.L. Michelotti, J. Chem. Soc. Chem.
Commun. (1979) 637.
[6] H. Okamura, M. Miura, H. Takei, Tetrahedron Lett. (1979) 43.
[7] H. Okamura, H. Takei, Tetrahedron Lett. (1979) 3425.
[8] J. Gerard, E. Bietlot, L. Hevesi, Tetrahedron Lett. 39 (1998) 8735.
[9] H. Okamura, M. Miura, K. Kosugi, H. Takei, Tetrahedron Lett.
(1980) 87.
ing to the GCÁ
/
MS 3b (219 mg, 78% yield), (Z)-
EtSeCHÄCHBu (42 mg, 11% yield), 1-butanol (41
/
mg), n-octane (226 mg) and EtSeSeEt (145 mg).
Separation of the mixture was performed by column
chromatography (silicagel L5/40, eluents: successively
hexane, CHCl3 and acetone).
[10] S. Uemura, Sh. Fukuzawa, S.R. Patil, J. Organometal. Chem. 243
(1983) 249.
[11] V.A. Potapov, S.V. Amosova, A.A. Starkova, A.R. Zhnikin, I.V.
Doron’kina, I.P. Beletskaya, L. Hevesi, Sulfur Lett. 23 (2000) 229.
[12] V.A. Potapov, S.V. Amosova, V.Yu. Shestakova, A.A. Starkova,
A.R. Zhnikin, Sulfur Lett. 21 (1998) 103.
3.3. The NiCl2(dppe)-catalyzed cross-coupling of (Z)-
1,2-bis(ethylseleno)ethene (1) with phenyl magnesium
bromide (2d)
[13] V.A. Potapov, S.V. Amosova, I.P. Beletskaya, A.A. Starkova, L.
Hevesi, Phosphorus, Sulfur, Silicon Relat. Elem. 136Á138 (1998)
/
591.
[14] G.T. Crisp, M.P. Collis, Aust. J. Chem. 41 (1988) 935.
Analogously to the procedure described for 2c, the
ethene 1 (484 mg, 2 mM), NiCl2(dppe) (54 mg, 0.1 mM),
and 10 ml of the 0.92 N ether solution of phenyl
magnesium bromide (2d) (9.2 mM) were reacted. The
residue after the evaporation in vacuo contains accord-
[15] H.O. House, E.F. Kinloch, J. Org. Chem. 39 (1974) 747.
[16] S.-I. Murahashi, M. Yamamura, K.-I. Yanagasiwa, N. Mita, K.
Kondo, J. Org. Chem. 44 (1979) 2408.
[17] Ei-ichi Negishi, Kuen-Wai Chiu, J. Org. Chem. 41 (1976) 3484.
[18] M. Huhtasaari, H.J. Schaefer, H. Luftmann, Acta Chem. Scand.
Ser. B. 37 (1983) 537.
ing to the GCÁMS unconverted 1 (89 mg, 82% conver-
/
sion), 2-ethylseleno styrene (4) (73% yield on the ethene
1 reacted), diphenyl (186 mg) and 1-phenylethanol (93
mg). Separation of the mixture was performed by
column chromatography (silicagel L5/40, eluents: suc-
cessively hexane, CHCl3 and acetone).
[19] V.I. Bykov, T.A. Butenko, E. Sh. Finkel’shtein, Bull. Acad. Sci.
USSR Div. Chem. Sci. (Engl. Transl.) 39 (1990) 151.
[20] A. Krief, L. Hevesi, J.B. Nagy, E.G. Deroune, Angew. Chem. 89
(1977) 103.
[21] D.E. Dorman, M. Jautelat, J.D. Roberts, J. Org. Chem. 36 (1971)
2757.
[22] V.A. Potapov, S.V. Amosova, Phoshorus Sulfur Silicon Relat.
Elem. 79 (1993) 277.
References
[23] M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, M. Monta-
nucci, Tetrahedron Lett. 25 (1984) 4975.
[24] L. Testaferri, M. Tiecco, M. Tingoli, D. Chianelli, Tetrahedron 41
(1985) 1401.
[1] I.P. Beletskaya, C. Moberg, Chem. Rev. 99 (1999) 3435 (refer-
ences cited therein).