PALLADIUM-CATALYZED REACTIONS OF VINYL BROMIDES WITH DISUBSTITUTED ALKYNES - A NEW SYNTHESIS OF FULVENES

被引：34

作者：

SILVERBERG, LJ ^{[1
]}

WU, GZ ^{[1
]}

RHEINGOLD, AL ^{[1
]}

HECK, RF ^{[1
]}

机构：

[1] UNIV DELAWARE,DEPT CHEM,CTR CATALYT SCI & TECHNOL,NEWARK,DE 19716

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1991年 / 409卷 / 03期

关键词：

D O I：

10.1016/0022-328X(91)80026-G

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100-degrees-C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reactions of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.

引用

页码：411 / 420

页数：10

共 38 条

[1] ALPER H, 1980, SYNTHESIS-STUTTGART, P799
[2] SYNTHESIS OF FULVENES BY REACTION OF THIOBENZOPHENONES WITH CYCLOPENTADIENYLMETAL CARBONYL ANIONS UNDER ANHYDROUS OR PHASE TRANSFER CATALYZED CONDITIONS
ALPER, H
PAIK, HN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (02) : 508 - 512
[3] ARTHURS M, 1982, ADV ORGANOMET CHEM, V21, P1
[4] BAILEY PM, 1976, J CHEM SOC CHEM COMM, V7, P238
[5] 1,2,3,4,6-PENTAMETHYLFULVENE - A CONVENIENT PRECURSOR TO SUBSTITUTED TETRAMETHYLCYCLOPENTADIENYL TRANSITION-METAL COMPLEXES
BENSLEY, DM
MINTZ, EA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 353 (01) : 93 - 102
[6] FULVENES AND SUBSTITUTED FULVENES
BERGMANN, ED
[J]. CHEMICAL REVIEWS, 1968, 68 (01) : 41 - &
[7] PENTAFULVENES - VERSATILE SYNTHONS IN METALLOCENE CHEMISTRY
BICKERT, P
HILDEBRANDT, B
HAFNER, K
[J]. ORGANOMETALLICS, 1984, 3 (05) : 653 - 657
[8] REACTIONS OF PALLADIUM COMPOUNDS WITH ACETYLENES .1. TETRAPHENYLCYCLOBUTADIENEPALLADIUM(II) CHLORIDE
BLOMQUIST, AT
MAITLIS, PM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (12) : 2329 - &
[9] BONAGURA HG, 1954, J AM CHEM SOC, V76, P6125
[10] A SIMPLE TOTAL SYNTHESIS OF VIBURTINAL
BRAYER, JL
ALAZARD, JP
THAL, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) : 257 - 258

← 1 2 3 4 →