ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .77. 2-BUTENE-1,4-DIONES BY PHOTOINDUCED ACYL MIGRATION OF ([2-(ACYLOXY)ETHENYL]CARBENE)CHROMIUM COMPLEXES

被引:8
作者
AUMANN, R
JASPER, B
机构
[1] Organisch-Chemisches Institut der Uniuersität Münster, D-48149 Münster
关键词
D O I
10.1021/om00003a055
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Photolysis of [(Z)-2-(acyloxy)ethenyl]carbene complexes (CO)(5)Cr=C(OEt)CH=C(OCOR(1))R [(Z)-3] (R = C6H5, t-Bu, c-Pr; R(1) = C6H5, c-Pr, c-C7H7CH2, t-Bu, Me(2)C=CH) with UV light of >300 nm affords 2-butene-1,4-diones R(1)COC(OEt)=CHCOR [(E)-6] (60-68%), by a novel metal-mediated acyl migration. Compounds (Z)-6 and furans 7 are formed as minor products.
引用
收藏
页码:1461 / 1465
页数:5
相关论文
共 60 条
[1]   DIRECT PHOTOLYSIS AND ELECTRON-TRANSFER PHOTOOXYGENATION OF ENOL ACETATES OF 3-PHENYLPROPIOPHENONES [J].
ALGARRA, F ;
BALDOVI, MV ;
GARCIA, H ;
MIRANDA, MA ;
PRIMO, J .
MONATSHEFTE FUR CHEMIE, 1993, 124 (02) :209-215
[2]  
ALVEREZTOLEDANO C, 1987, J ORGANOMET CHEM, V323, P371
[3]  
AUMANN R, 1994, SYNLETT, P1041
[4]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .72. (2-(ACYLOXY)ETHENYL)CARBENE COMPLEXES BY MICHAEL ADDITION OF CARBOXYLIC-ACIDS TO ALKYNYLCARBENE COMPLEXES (M=CR, W) - (2-(ACYLOXY)ETHENYL)KETENE IMINES BY LIGAND DISENGAGEMENT WITH ISOCYANIDE [J].
AUMANN, R ;
JASPER, B ;
LAGE, M ;
KREBS, B .
ORGANOMETALLICS, 1994, 13 (09) :3502-3509
[5]   KETENIMINE COMPLEXES FROM CARBENE COMPLEXES AND ISOCYANIDES - VERSATILE BUILDING-BLOCKS FOR CARBOCYCLES AND N-HETEROCYCLES [J].
AUMANN, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (11) :1456-1467
[6]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .57. 4,5-HOMOTROPILIDENES BY INTRAMOLECULAR CYCLOPROPANATION OF (CYCLOHEPTATRIENYLMETHYL)CARBENECHROMIUM OR (CYCLOHEPTATRIENYLMETHYL)CARBENETUNGSTEN COMPLEXES [J].
AUMANN, R ;
RUNGE, M .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (01) :259-264
[7]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .47. 1-CHROMA-1,3-DIENES BY AMINOALKENYLATION OF METHYLCARBENE CHROMIUM COMPLEXES WITH SECONDARY AMIDES [J].
AUMANN, R ;
HINTERDING, P .
CHEMISCHE BERICHTE, 1990, 123 (10) :2047-2051
[8]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .69. 2-(ACYLAMINO)ETHENYL KETENE IMINES FROM [2-(ACYLAMINO)ETHENYL]CARBENE COMPLEXES AND THEIR RING-CLOSING METATHESIS TO PYRROLES OR ELECTROCYCLIZATION TO 1,4-DIAMINONAPHTHALENES [J].
AUMANN, R ;
JASPER, B ;
GODDARD, R ;
KRUGER, C .
CHEMISCHE BERICHTE, 1994, 127 (04) :717-724
[9]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .2. 1-CHROMA-1,3-BUTADIENES AND 1-CHROMA-1,3,5-HEXATRIENES FROM (CO)5CR=C(OC2H5)CH3 BY CARBONYL OLEFINATION CATALYZED WITH TRIETHYLAMINE CHLOROTRIMETHYLSILANE [J].
AUMANN, R ;
HEINEN, H .
CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (04) :537-540
[10]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .73. ACYLATION OF METHYLCARBENE COMPLEXES (M=CR, W) WITH FORMATION OF [2-(ACYLOXY)ETHENYL]CARBENE, [4-(ACYLOXY)BUTADIENYL]CARBENE, AND ALKYNYLCARBENE COMPLEXES [J].
AUMANN, R ;
JASPER, B ;
LAGE, M ;
KREBS, B .
ORGANOMETALLICS, 1994, 13 (09) :3510-3516