REACTION OF (Z)-(PHENYLVINYL)ACETYLENES AND (Z)-(CYCLOPROPYLVINYL)ACETYLENES WITH FISCHER CARBENE-CHROMIUM COMPLEXES - AN ALTERNATIVE APPROACH TO BENZANNULATION AND CYCLOPENTANNULATION

被引:33
作者
HERNDON, JW
HAYFORD, A
机构
[1] Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland
关键词
D O I
10.1021/om00004a005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of (Z)-(phenylvinyl)acetylenes and carbene complexes provides benzannulation products in fair to good yields. Similarly, the reaction of (Z)-(cyclopropylvinyl)acetylenes and carbene complexes provides cyclopentenone derivatives. When the carbene complex is capable of further ring-forming reactions, subsequent ring-forming steps occur preferentially from the substituent on the enyne.
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页码:1556 / 1558
页数:3
相关论文
共 20 条
[1]   INTRAMOLECULAR REACTIONS OF FISCHER CARBENE COMPLEXES WITH ALKYNES AND A MECHANISTIC STUDY OF THE INTERCEPTION OF REACTIVE INTERMEDIATES WITH ADDED ACETYLENES [J].
ANDERSON, BA ;
BAO, JM ;
BRANDVOLD, TA ;
CHALLENER, CA ;
WULFF, WD ;
XU, YC ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :10671-10687
[2]   CHARACTERIZATION OF THE 1ST ETA-4-VINYLKETENE METAL-COMPLEX FROM THE REACTION OF A GROUP-6 FISCHER CARBENE COMPLEX AND AN ALKYNE [J].
ANDERSON, BA ;
WULFF, WD ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8615-8617
[3]   ANNULATION REACTION OF VINYLALMINOCARBENES - CHARACTERIZATION OF THE TETRACARBONYL VINYLCARBENE AND METALAHEXATRIENE INTERMEDIATES [J].
BARLUENGA, J ;
AZNAR, F ;
MARTIN, A ;
GARCIAGRANDA, S ;
PEREZCARRENO, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11191-11192
[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]   TOTAL SYNTHESIS OF THE HOST DEFENSE STIMULANT MAESANIN [J].
DANHEISER, RL ;
CHA, DD .
TETRAHEDRON LETTERS, 1990, 31 (11) :1527-1530
[6]   METALLACYCLOBUTENE METALLABUTADIENE (VINYLCARBENE COMPLEX) INTERCONVERSIONS - RING-OPENING OF TITANACYCLOBUTENES [J].
DOXSEE, KM ;
JULIETTE, JJJ ;
MOUSER, JKM ;
ZIENTARA, K .
ORGANOMETALLICS, 1993, 12 (12) :4742-4744
[7]   REACTIONS OF COMPLEX LIGANDS .45. (ACYLAMINO)CARBENE COMPLEXES - SYNTHESIS, STRUCTURE, AND REACTIVITY [J].
GROTJAHN, DB ;
KROLL, FEK ;
SCHAFER, T ;
HARMS, K ;
DOTZ, KH .
ORGANOMETALLICS, 1992, 11 (01) :298-310
[8]  
HOFMANN P, 1991, NEW J CHEM, V15, P769
[9]  
HOYE TR, 1989, ORGANOMETALLICS, V8, P2071
[10]   A SYNTHESIS OF HIGHLY SUBSTITUTED AROMATICS THROUGH REGIOCONTROLLED CONSTRUCTION OF CYCLOBUTENONES BEARING UNSATURATED SUBSTITUENTS AT THE 4-POSITION [J].
KRYSAN, DJ ;
GURSKI, A ;
LIEBESKIND, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1412-1418