Abstract
The addition of trimethylsilyl cyanide (TMSCN) to diacylferrocenes [Fc (COR)2] (R = Me, Et, Ph, p-ClC6H4, m-ClC6H4, o-ClC6H4, p-MeOC6H4, Fc = C5H4FeC5H4), catalysed by zinc iodide an acetonitrile provided the corresponding cyanohydrin trimethylsilyl ethers in moderate to high yields. Factors affecting the reaction and yields of adducts were investigated. In addition, the adduct of 1,1′-diacetylferrocene was structurally determined by X-ray crystallography.
References
1.
Gregory R.J.H.
, Chem. Rev. , 1999 , 99 , 3649 .
2.
(a)
Hünig S.
, and
Wehner G.
, Synthesis , 1979 , 522 ; (b) J.W. Zubric, B.I. Dunbar and H.D. Durst, Tetrahedron Lett. , 1975, 1 , 71.
3.
(a)
Faller J.W.
, and
Gundersen L.L.
, Tetrahedron Lett. , 1993 , 34 , 2275 ; (b) M.T. Reetz and D.N.A. Fox, Tetrahedron Lett. , 1993, 34 , 1119; (c) T. Miurra and Y. Masaki, Chem. Soc. P.T.I. , 1994, 1659; (d) S. Matthias and C. Fu. Gregory, J. Org. Chem. , 1994, 59 , 7178; (e) J.K. Whitesell and R. Apodaca, Tetrahedron Lett. , 1996, 37 , 2525; (f) H. Quast, Y. Görlach and E.M. Peters, Chem. Ber. , 1986, 119 , 1801; (g) H.S. Wilkinson, P.T. Grover and C.P. Vandenbossche, Org. Lett. , 2001, 3 , 553.
4.
(a)
Liang S.
, and
Bu X.R.
, J. Org. Chem. , 2002 , 67 , 2702 ; (b) Y. Hamashima, M. Kanai and M. Shibasaki, J. Am. Chem. Soc. , 2000, 122 , 7412.
5.
Bian Z.X.
,
Zhao H.Y.
, and
Li B.G.
, Polyhedron , 2003 , 22 , 1523 .
6.
(a)
Evans D.A.
,
Treadle L.K.
, and
Carroll G.L.
, J. Chem. S. Chem. Commun. , 1973 , 55 ; (b) D.A. Evans, G.L. Carroll and L.K. Truesdale, J. Org. Chem. , 1974, 39 , 914; (c) D.A. Evans and L.K. Truesdale, Tetrahedron Lett. , 1973, 49 , 4929; (d) M. Wada, T, Takahashi and T. Domae, Tetrahedron Asymm. , 1997, 8 , 3939; (e) J.K. Rasmussen and S.M. Heilmann, Synthesis , 1978, 219.
7.
Wang Y.X.
,
Bian Z.X.
, and
Zhao Q.H.
, Chin. J. Appl. Chem. , 2002 , 19 , 950 .
8.
Carey F.A.
, and
Sundberg R.J.
, Advanced Organic Chemistry (A) , Plenum Press , New York and London , 1984 . p. 202