Cationic platinum-complex-catalyzed skeletal reorganization of enynes

被引：126

作者：

Oi, S ^{[1
]}

Tsukamoto, I ^{[1
]}

Miyano, S ^{[1
]}

Inoue, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Engn, Dept Chem Mat, Aoba Ku, Sendai, Miyagi 9808579, Japan

来源：

ORGANOMETALLICS | 2001年 / 20卷 / 17期

关键词：

D O I：

10.1021/om010316v

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The skeletal reorganization of 1,6-enynes into 1-vinylcyclopentenes was catalyzed by a cationic platinum complex under extremely mild conditions. The unusual rearrangement of the carbon skeleton, involving the cleavage of both the double and triple carbon-carbon bonds, was observed in certain cases and confirmed by C-13- and H-2-labeling experiments. Reaction mechanisms describing the rearrangement of carbocations are proposed.

引用

页码：3704 / 3709

页数：6

共 22 条

[1] THE PREPARATION OF ORGANOIRON ETA-1-ALPHA-ALKOXYETHYL COMPLEXES AND THEIR REACTION WITH ELECTROPHILES - CHARACTERIZATION OF CATIONIC ORGANOIRON ETHYLIDENE COMPOUNDS
BODNAR, T
CUTLER, AR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 213 (02) : C31 - C36
[2] SYNTHESIS, SPECTRAL CHARACTERIZATION, AND ALKYLIDENE TRANSFER-REACTIONS OF ELECTROPHILIC IRON CARBENE COMPLEXES CP(CO)(L)FE=CHR+,L=CO,P(C6H5)3,R=CH3,CH2CH3,CH(CH3)2
BROOKHART, M
TUCKER, JR
HUSK, GR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (02) : 258 - 264
[3] SYNTHESIS OF ELECTROPHILIC (DIMETHYLCARBENE) IRON COMPLEXES
CASEY, CP
MILES, WH
TUKADA, H
OCONNOR, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) : 3761 - 3762
[4] SYNTHESIS, CHARACTERIZATION, AND REACTIONS OF (C5H5)(CO)2FE=C(CH3)2+ AND (C5H5)(CO)2FE=CH-CH=C(CH3)2+
CASEY, CP
MILES, WH
TUKADA, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) : 2924 - 2931
[5] Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes
Chatani, N
Kataoka, K
Murai, S
Furukawa, N
Seki, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) : 9104 - 9105
[6] PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes
Chatani, N
Furukawa, N
Sakurai, H
Murai, S
[J]. ORGANOMETALLICS, 1996, 15 (03) : 901 - 903
[7] HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2)
CHATANI, N
MORIMOTO, T
MUTO, T
MURAI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) : 6049 - 6050
[8] Ru3(CO)12-catalyzed cyclocarbonylation of yne-aldehydes to bicyclic α,β-unsaturated γ-butyrolactones
Chatani, N
Morimoto, T
Fukumoto, Y
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) : 5335 - 5336
[9] CATIONIC METAL-CARBENE COMPLEXES IN CYCLOADDITION REACTIONS - SYNTHESIS AND REACTIONS OF IRON-CYCLOPROPYL COMPLEXES
CUTLER, A
ROSENBLU.M
GIERING, WP
FISH, RW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4354 - &
[10] Novel rearrangements of enynes catalyzed by PtCl2
Fürstner, A
Szillat, H
Stelzer, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6785 - 6786

← 1 2 3 →