REACTION OF METAL CARBENE COMPLEXES WITH CYCLOBUTENEDIONES - THE 1ST GENERAL C-C BOND INSERTION REACTION FOR FISCHER CARBENE COMPLEXES

被引:28
作者
ZORA, M [1 ]
HERNDON, JW [1 ]
机构
[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLL PK,MD 20742
关键词
D O I
10.1021/om00026a002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Alkylcarbene-chromium complexes react with cyclobutenediones to give 2-alkoxy-4-cyclopentene-1,3-diones in moderate yield, accompanied by varying amounts of 4-cyclopentene-1,3-dione derivatives which result from reduction of the initial product by the chromium byproduct. The reaction is general for a variety of cyclobutenedione derivatives with alkoxy, alkyl, or aryl substituents. The major products of the reaction between arylcarbene complexes and cyclobutenediones are 5-alkylidenefuranone derivatives. A mechanism involving oxidative addition of the acyl-acyl C-C bond, followed by carbene insertion and reductive elimination, is proposed.
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页码:248 / 249
页数:2
相关论文
共 20 条
[1]   METABOLITES OF THE HIGHER FUNGI .19. SERPENONE, 3-METHOXY-4-METHYL-5-PROP-1-ENYLFURAN-2(5H)-ONE, A NEW GAMMA-BUTYROLACTONE FROM THE FUNGUS HYPOXYLON-SERPENS (BARRONS STRAIN) (PERSOON EX FRIES)KICKX [J].
ANDERSON, JR ;
EDWARDS, RL ;
WHALLEY, AJS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :215-221
[2]  
Brown F. J., 1980, PROG INORG CHEM, V27, P1
[3]   SYNTHESIS OF (E)-PULVINONES AND (Z)-PULVINONES [J].
CAMPBELL, AC ;
MAIDMENT, MS ;
PICK, JH ;
STEVENSON, DFM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1567-1576
[4]  
Claisen L., 1895, LIEBIGS ANN CHEM, V284, P245
[5]   TRANSITION-METAL CARBENE COMPLEXES .53. PROOF OF ABSENCE OF A FREE CARBENE IN PREPARATION OF A CYCLOPROPANE FROM A METAL-CARBENE COMPLEX [J].
COOKE, MD ;
FISCHER, EO .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 56 (AUG1) :279-284
[6]   CARBENE COMPLEXES IN ORGANIC-SYNTHESIS [J].
DOTZ, KH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :587-608
[7]   SYNTHESIS OF BICYCLOPROPYL DERIVATIVES FROM THE REACTION OF CYCLOPROPYLCARBENE-CHROMIUM COMPLEXES WITH ALKENES [J].
HERNDON, JW ;
TUMER, SU .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :286-294
[8]   A FORMAL 4 + 1 ROUTE TO ALKYLIDENE CYCLOPENTENEDIONES - A SYNTHETIC APPLICATION OF THE TRANSITION-METAL-CATALYZED TERMINAL ALKYNE REVERSIBLE VINYLIDENE REARRANGEMENT [J].
LIEBESKIND, LS ;
CHIDAMBARAM, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :5025-5026
[9]   AN IMPROVED METHOD FOR THE SYNTHESIS OF SUBSTITUTED CYCLOBUTENEDIONES [J].
LIEBESKIND, LS ;
FENGL, RW ;
WIRTZ, KR ;
SHAWE, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2482-2488
[10]  
LIEBESKIND LS, 1984, J AM CHEM SOC, V106, P6450