Abstract
The reduction of diselenides by samarium diiodide led to samarium selenolates (RSeSmI2). These species reacted with 3-substituted-1-chlorocarbonyl-imidazolidin-2-ones to give the corresponding selenoesters in good yields under mild and neutral conditions.
References
1.
Patai S.
, and
Rappoport Z.
(eds) The Chemistry of Organic Selenium, and Tellurium Compound , John Wiley , Chichester England , Vol. 1 ., 1986 .
2.
Ogawa A.
, and
Sonoda N.
, in Comprehensive Organic Synthesis ed. by
Trost B.M.
Pergamon Press Oxford , Vol. 6 , pp. 461 , 1991 .
3.
Sviridov A.F.
,
Ermolenko M.S.
,
Yashunsky D.V.
, and
Kochethov N.K.
, Tetrahedron Lett. , 1983 , 24 , 4355 .
4.
Kozikowski A.P.
, and
Ames A.
, J. Am. Chem. Soc. , 1980 , 102 , 860 .
5.
Grieco P.A.
,
Yokoyama Y.
, and
Williams E.
, J. Org. Chem. , 1978 , 43 , 1283 .
6.
(a)
Pfenninger J.
,
Heuberger C.
, and
Graf W.
, Helv. Chim. Acta. , 1980 , 63 , 2328
7.
Boger D.L.
, and
Mathvink R.J.
, J. Org. Chem. , 1992 , 57 , 1429
8.
Batty D.
, and
Crich D.
, J. Chem. Soc., Perkin. Trans. 1 , 1992 , 3193, 3205 .
9.
(a)
Uemura S.
,
Takahashi H.
,
Ohe K.
, and
Sugita N.
, J. Organoment. Chem. , 1989 , 361 , 63
10.
Kuniyasu H.
,
Ogawa A.
,
Miyazaki S.
,
Ryu I.
,
Kambe N.
, and
Sonoda N.
, J. Am. Chem. Soc. , 1991 , 113 , 9796
11.
Inoue T.
,
Takeda T.
,
Kambe N.
,
Ogawa A.
,
Ryu I.
, and
Sonoda N.
, J. Org. Chem. , 1994 , 59 , 5824
12.
Kawahara Y.
,
Kato S.
,
Kanda T.
, and
Murai T.
, Bull. Chem. Soc. Jpn. , 1994 , 67, 1881 .
13.
Liu Y.
, and
Zhang Y.
, Synth. Commun. , 1999 , 29 , 4043 .
14.
For review see: (a)
Kagan H.B.
, and
Namy J.L.
, Tetrahedron , 1986 , 42 , 1725
15.
Molander G.A.
, Chem. Rev. , 1992 , 92 , 29
16.
Molander G.A.
, and
Harris C.R.
, Chem. Rev. , 1996 , 96 , 307
17.
Yu M.
,
Zhang Y.
, and
Bao W.
, Chin. J. Chem. , 1999 , 17 , 4 .
18.
Girard P.
,
Namy J.L.
, and
Kagan H.B.
, J. Am. Chem. Soc. , 1980 , 102 , 2693 .
19.
Zhang Y.
,
Yu Y.
, and
Lin R.
, Synth. Commun. , 1993 , 23 , 189 .
20.
Su W.
, and
Zhang Y.
, J. Chem. Research(S) , 2000 , 440 .
