Preparation of 3-oxocyclohex-1-ene-1-carbonitrile

被引:11
作者
Fleming, FF [1 ]
Zhang, ZY [1 ]
Wei, GQ [1 ]
机构
[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA
来源
SYNTHESIS-STUTTGART | 2005年 / 18期
关键词
oxonitrile; nitrite; oxidation; synthesis;
D O I
10.1055/s-2005-872177
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chromium trioxide oxidation of cyclohexenecarbonitrile efficiently provides analytically pure 3-oxocyclohex-1-ene-1-carbonitrile. The procedure is described in detail, providing a very reliable, one-step synthesis of a highly versatile oxonitrile.
引用
收藏
页码:3179 / 3180
页数:2
相关论文
共 22 条
[1]   SYNTHESIS AND PHOTOCYCLOADDITIONS OF COMPOUNDS RELATED TO 3-CARBOXYCLOHEXENONE [J].
AGOSTA, WC ;
LOWRANCE, WW .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3851-&
[3]   PHOTOCHEMICAL TRANSFORMATIONS OF SOME BETA-SUBSTITUTED ENONES [J].
CANTRELL, TS .
TETRAHEDRON, 1971, 27 (06) :1227-&
[4]   Dirhodium(II) caprolactamate: An exceptional catalyst for allylic oxidation [J].
Catino, AJ ;
Forslund, RE ;
Doyle, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13622-13623
[5]   THE MONOETHYLENE KETAL OF 1,3-CYCLOHEXANEDIONE [J].
CRONYN, MW ;
GOODRICH, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (13) :3331-3333
[6]   Metalated nitriles: Electrophile-dependent alkylations [J].
Fleming, FF ;
Zhang, ZY ;
Wei, GQ ;
Steward, OW .
ORGANIC LETTERS, 2005, 7 (03) :447-449
[7]   Oxonitriles: Multicomponent grignard addition-alkylations [J].
Fleming, FF ;
Zhang, ZY ;
Wang, QZ ;
Steward, OW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1126-1129
[8]   Hydroxy alkenenitriles: Diastereoselective conjugate addition-alkylations [J].
Fleming, FF ;
Wang, QZ ;
Steward, OW .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4235-4238
[9]  
JOHNSON JN, 1995, ENCY REAGENTS ORGANI, V2, P1275
[10]  
KURIHARA T, 1986, CHEM PHARM BULL, V34, P2747