Abstract
The Se–Se bond in diselenides was reduced by Zn/ZrCl4 to produce selenolate anions, which react with α,β -unsaturated esters or α,β -unsaturated nitriles to afford β-selenoesters and β-selenonitriles, respectively.
Keywords
References
1.
Peich H.T.
, Acc. Chem. Res. , 1979 , 12 , 22 .
2.
Kato S.
,
Murai T.
, and
Masura M.
, Org. Prep. Proced. Int. , 1986 , 18 , 369 .
3.
Perrick L.T.
, Tetrahedron , 1978 , 34 (8 ), 1049 .
4.
Griceo P.A.
,
Yokoyama Y.
, and
Williams E.
, J. Org. Chem. , 1978 , 43 , 1283 .
5.
Kataev E.G.
, and
Gabdrakhmanav F. G.
, Zh. Obshch. Khim. , 1967 , 37 , 772 .
6.
Miyashita M.
, and
Yoshikashi A.
, Synthesis , 1980 , 8 , 664 .
7.
Jiang H.
, and
Zhang Y.
, Hecheng Huaxue , 1993 , 3 , 248 .
8.
Ogawa A.
,
Nishiyama Y.
,
Kambe N.
,
Murai S.
, and
Sonoda N.
, Tetrahedron Lett. , 1987 , 28 , 3271 .
9.
(a)
Cho Y.S.
,
Lee J. E.
,
Pae A. N.
,
Choi K. I.
, and
Koh H. Y.
, Tetrahedron Lett. , 1999 , 40 , 1725 .
10.
Renaud J.L.
,
Aubert C.
, and
Malacria M.
, Tetrahedron Lett. , 1999 , 40 , 5015 .
11.
Bieber L.W.
,
Silva M. F.
,
Costa R. C.
, and
Silva L. O. S.
, Tetrahedron Lett. , 1998 , 39 , 3655 .
12.
Rubasam F.
,
Seek S.
, and
Giannis A.
, Tetrahedron , 1997 , 52 , 2823 . (e) D. Wang, L. Dai, X. Hou, and Y. Zhang, Tetrahedron Lett. , 1996, 37 , 4187.
13.
Wang Z.
, and
Hammond G. B.
, Tetrahedron Lett. , 2000 , 41 , 2339 .
14.
Kim S.H.
, and
Ham E. H.
, Tetrahedron Lett. , 2000 , 41 , 6479 .
15.
(a)
Handa T.C.
, and
Inanaga J. J.
, Tetrahedron Lett. , 1987 , 28 , 5717 .
16.
McMurry J.E.
, Chem. Rev. , 1989 , 89 , 1513 .
17.
Dutta D.K.
, and
Konwar D.
, Tetrahedron Lett. , 2000 , 41 , 6227 .
18.
Chen J.
,
Li J.
,
Yu M.
, and
Chen W.
Org. Prep. Proced. Int. , 1997 , 29 , 569 .
19.
So J.H.
,
Park M. K.
, and
Boudjouk P.
, J. Org. Chem. , 1988 , 53 , 5871 .
20.
Lioaki T.A.
,
Hilfiker M. A.
, and
Nelson S.
, J. Org. Chem. , 1997 , 62 , 4566 .
21.
(a)
Kitagawa O.
,
Takeo T.
, and
Kobayashi Y.
, Tetrahedron Lett. , 1988 , 29 , 1803 .
22.
Qian Kyoung Soon Kim Ligang
, Tetrahedron Lett. , 1993 , 34 , 7195 .
23.
Andres Jose M
, Refael Pedrosa and Alfonso Perez-Encabo , Tetrahedron , 2000 , 56 , 1217 .
24.
Zhang S.
, and
Zhang Y.
, Chinese Chem. Lett. , 1998 , 9 , 885 .
