INSERTION OF FISCHER CARBENE COMPLEXES INTO THE CARBON-CARBON BOND OF 1,2-DIPHENYLCYCLOPROPENONE - FORMATION OF CYCLOBUTENONES AND O-METHOXYPHENOL AND P-METHOXYPHENOL DERIVATIVES

被引:19
作者
ZORA, M [1 ]
HERNDON, JW [1 ]
机构
[1] UNIV MARYLAND, DEPT CHEM & BIOCHEM, COLLEGE PK, MD 20742 USA
关键词
D O I
10.1021/om00020a059
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction between 1,2-diphenylcyclopropenone and Fischer carbene complexes has been investigated. The reaction produced a mixture of diphenylacetylene and cyclobutenones. When alpha,beta-unsaturated carbene complexes were employed, benzannulation products and diphenylacetylene, were produced. A mechanism involving metallacyclobutenone formation, followed by either carbene insertion and reductive elimination or fragmentation has been proposed.
引用
收藏
页码:3370 / 3373
页数:4
相关论文
共 28 条
[1]   REACTIONS OF DIPHENYLCYCLOPROPENONE WITH KETENES IN PRESENCE OF NICKEL TETRACARBONYL [J].
BABA, A ;
OHSHIRO, Y ;
AGAWA, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 110 (01) :121-127
[2]  
BILLUPS WE, 1987, CHEM CYCLOPROPYL GRO, pCH24
[3]   ORGANOMETALLIC INTERMEDIATES .3. REACTIONS OF CYCLOPROPENONES WITH IRON AND COBALT CARBONYLS [J].
BIRD, CW ;
BRIGGS, EM ;
HUDEC, J .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (19) :1862-+
[4]   SUBSTRATE REGULATION OF PRODUCT DISTRIBUTION IN THE REACTIONS OF ARYL CHROMIUM CARBENE COMPLEXES WITH ALKYNES [J].
BOS, ME ;
WULFF, WD ;
MILLER, RA ;
CHAMBERLIN, S ;
BRANDVOLD, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9293-9319
[5]  
Casey C. P., 1985, REACTIVE INTERMEDIAT, V3, P109
[6]  
CASEY CP, 1981, REACTIVE INTERMEDIAT, V2, P135
[7]   SOLVENT, CHELATION AND CONCENTRATION EFFECTS ON THE BENZANNULATION REACTION OF CHROMIUM CARBENE COMPLEXES AND ACETYLENES [J].
CHAN, KS ;
PETERSON, GA ;
BRANDVOLD, TA ;
FARON, KL ;
CHALLENER, CA ;
HYLDAHL, C ;
WULFF, WD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (1-2) :9-56
[8]  
CHONG KS, 1982, ORGANOMETALLICS, V1, P1586, DOI 10.1021/om00072a007
[9]   REACTIONS OF COMPLEX LIGANDS .9. CARBENE LIGANDS, CARBONYL LIGANDS AND ALKYNES AS UNITS FOR ISOCYCLIC AND HETEROCYCLIC-SYSTEMS [J].
DOTZ, KH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 140 (02) :177-186
[10]   CARBONYL-CARBENE COMPLEXES AS BIFUNCTIONAL REAGENTS - TRANSFER OF ALKYNES IN CYCLOBUTENONES [J].
DOTZ, KH ;
DIETZ, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 157 (04) :C55-C57