INTRAMOLECULAR INTERCONVERSION OF SYN-TRICARBONYL(1-ETHOXY-1,2-DIHYDROCYCLOBUTABENZENE)CHROMIUM AND ANTI-TRICARBONYL(1-ETHOXY-1,2-DIHYDROCYCLOBUTABENZENE)CHROMIUM - TRAPPING OF THE ORTHO-QUINODIMETHANE INTERMEDIATE

被引:31
作者
KUNDIG, EP [1 ]
BERNARDINELLI, G [1 ]
LERESCHE, J [1 ]
ROMANENS, P [1 ]
机构
[1] UNIV GENEVA,CRYSTALLOG LAB,CH-1211 GENEVA 4,SWITZERLAND
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 04期
关键词
D O I
10.1002/anie.199004071
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reversible isomerization of syn‐1 to anti‐1 occurs without cleavage of metal‐ligand bonds, as demonstrated through a [4 + 2] cycloaddition with trans‐1,2‐bis(trimethylsilyl)ethene as the dienophile, which led to the trapping of an ortho‐quinodimethane intermediate. Further evidence comes from kinetic studies. Ring opening in 1 proceeds considerably more slowly than in the case of the non‐complexed analogue, a finding that can be explained by entropy effects. (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany
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页码:407 / 409
页数:3
相关论文
共 17 条
[1]   PHOTOCHEMICAL REACTIONS .3. THERMAL GENERATION OF PHOTOENOLS AND THEIR DERIVATIVES FROM SUBSTITUTED 1,2-DIHYDROBENZOCYCLOBUTENES [J].
ARNOLD, BJ ;
SAMMES, PG ;
WALLACE, TW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (03) :409-414
[2]   SYNTHESIS, STRUCTURE, AND BONDING OF FULVENE COMPLEXES OF TITANIUM, MOLYBDENUM, AND TUNGSTEN [J].
BANDY, JA ;
MTETWA, VSB ;
PROUT, K ;
GREEN, JC ;
DAVIES, CE ;
GREEN, MLH ;
HAZEL, NJ ;
IZQUIERDO, A ;
MARTINPOLO, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (10) :2037-2049
[3]   LEAST-SQUARES ABSOLUTE-STRUCTURE REFINEMENT - PRACTICAL EXPERIENCE AND ANCILLARY CALCULATIONS [J].
BERNARDINELLI, G ;
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1985, 41 (SEP) :500-511
[4]   REGIOSELECTIVE NUCLEOPHILIC ADDITIONS TO (ETA-6-BENZYL ALCOHOL)TRICARBONYLCHROMIUM - ISOLATION AND X-RAY CRYSTAL-STRUCTURE OF THE INTERMEDIATE (ETA-6-5-METHYLENE-6-EXO-TERT-BUTYLCYCLOHEXA-1,3-DIENE)TRICARBONYLCHROMIUM [J].
BLAGG, J ;
DAVIES, SG ;
GOODFELLOW, CL ;
SUTTON, KH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (16) :1283-1285
[5]   PROTON NMR-SPECTRA OF 1-SUBSTITUTED BENZOCYCLOBUTENES (BICYCLO[4,2,0]OCTA-1,3,5-TRIENES) [J].
BUBB, WA ;
STERNHELL, S .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (08) :1685-1697
[6]   ORTHOQUINODIMETHANES [J].
CHARLTON, JL ;
ALAUDDIN, MM .
TETRAHEDRON, 1987, 43 (13) :2873-2889
[7]   FR))NEW METHOD FOR CREATION OF SI-C BONDS FROM UNSATURATED HYDROCAR BONS - SUBSTITUTION OF ALLYL, VINYL OR PHENYL HYDROGEN [J].
DUNOGUES, J ;
CALAS, R ;
ARDOIN, N ;
BIRAN, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 32 (02) :C31-&
[8]   TRANSITION METAL-FULVENE COMPLEXES .26. DUAL REACTIVITY OF [ETA-5-(C5H4CHO)CR(CO)3]- ANIONS TOWARDS ELECTROPHILS - A NEW SYNTHESIS METHOD FOR FUNCTIONAL SUBSTITUTED CYCLOPENTADIENYL COMPLEXES AND (FULVENE)CR(CO)3-DERIVATIVES - MOLECULAR AND CRYSTAL-STRUCTURE OF (ETA-6-FULVENYLBENZOATE)CR(CO)3 AND (ETA-5-C5H4CHO)CR(CO)3AU(PPH3)T [J].
EDELMANN, F ;
TOFKE, S ;
BEHRENS, U .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 309 (1-2) :87-108
[9]   METAL PI-COMPLEXES OF BENZENE-DERIVATIVES .28. STRAINED ANELLATED ARENES AS PI-LIGANDS - SYNTHESIS AND MAGNETIC-RESONANCE PROPERTIES OF BIS(CYCLOBUTA-ETA-6-BENZENE)CHROMIUM0,+1 AND BIS([1,2-4,5]-DICYCLOBUTA-ETA-6-BENZENE)CHROMIUM0,+1 [J].
ELSCHENBROICH, C ;
KOCH, J ;
SCHNEIDER, J ;
SPANGENBERG, B ;
SCHIESS, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 317 (01) :41-54
[10]   NAPHTHALENE COMPLEXES .5. ARENE EXCHANGE-REACTIONS IN NAPHTHALENECHROMIUM COMPLEXES [J].
KUNDIG, EP ;
PERRET, C ;
SPICHIGER, S ;
BERNARDINELLI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (02) :183-200