REACTIONS OF ALKYNES AND CARBENE EQUIVALENTS WITH OXO(SALEN)CHROMIUM(V) COMPLEXES

被引：62

作者：

RIHTER, B ^{[1
]}

SRIHARI, S ^{[1
]}

HUNTER, S ^{[1
]}

MASNOVI, J ^{[1
]}

机构：

[1] CLEVELAND STATE UNIV,DEPT CHEM,CLEVELAND,OH 44115

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 10期

关键词：

D O I：

10.1021/ja00063a010

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkynes are oxidized by oxo(salen)chromium(V) triflate and related complexes 2 to form 1,2-diones. The oxidation of diphenylacetylene proceeds by formation of an intermediate which reacts more rapidly with a second equivalent of oxometal complex to form benzil. The intermediate is most likely a metallaoxetene or a related species, such as a metallocarbene. Reactions of phosphorus or nitrile ylides with 2 proceed to form carbonyl compounds (and phosphine oxide or nitrile) in a manner consistent with participation of similar intermediates. The reactions appear to be related mechanistically to alkene epoxidation by the same oxometal complexes.

引用

页码：3918 / 3924

页数：7

共 71 条

[1] ATHERTON SJ, 1984, J PHYS CHEM-US, V88, P2840, DOI 10.1021/j150657a034
[2] OXIRENES AND KETOCARBENES FROM ALPHA-DIAZOKETONE PHOTOLYSIS - EXPERIMENTS IN RARE-GAS MATRICES - RELATIVE STABILITIES AND ISOMERIZATION BARRIERS FROM MNDOC-BWEN CALCULATIONS
BACHMANN, C
NGUESSAN, TY
DEBU, F
MONNIER, M
POURCIN, J
AYCARD, JP
BODOT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) : 7488 - 7497
[3] ENHANCED SELECTIVITY BY AN OPEN-WELL EFFECT IN A METALLOPORPHYRIN-CATALYZED OXYGENATION REACTION
BORTOLINI, O
MEUNIER, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (12): : 1967 - 1970
[4] SUBSTRATE SELECTIVITY IN EPOXIDATION BY METALLOPORPHYRIN AND METALLOSALEN CATALYSTS CARRYING BINDING GROUPS
BRESLOW, R
BROWN, AB
MCCULLOUGH, RD
WHITE, PW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4517 - 4518
[5] ROOM-TEMPERATURE GENERATION OF REACTIVE INTERMEDIATES (CP-STAR)2-ZR=O AND (CP-STAR)2-ZR=S - TRAPPING REACTIONS WITH UNSATURATED ORGANIC-MOLECULES AND DATIVE LIGANDS
CARNEY, MJ
WALSH, PJ
BERGMAN, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6426 - 6428
[6] A REACTIVE ORGANOMETALLIC OXO INTERMEDIATE, (CP-STAR)2 ZR=O - GENERATION AND SUBSEQUENT TRAPPING REACTIONS FORMING ALKYNE AND NITRILE ADDITION-PRODUCTS
CARNEY, MJ
WALSH, PJ
HOLLANDER, FJ
BERGMAN, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) : 8751 - 8753
[7] INTERMEDIATES IN THE EPOXIDATION OF ALKENES BY CYTOCHROME-P-450 MODELS .1. CIS-STILBENE AS A MECHANISTIC PROBE
CASTELLINO, AJ
BRUICE, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) : 158 - 162
[8] EPOXIDATION OF OLEFINS BY CYTOCHROME-P-450 MODEL COMPOUNDS - KINETICS AND STEREOCHEMISTRY OF OXYGEN ATOM TRANSFER AND ORIGIN OF SHAPE SELECTIVITY
COLLMAN, JP
BRAUMAN, JI
MEUNIER, B
HAYASHI, T
KODADEK, T
RAYBUCK, SA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2000 - 2005
[9] OXYGENATION OF STYRENE BY CYTOCHROME-P-450 MODEL SYSTEM - A MECHANISTIC STUDY
COLLMAN, JP
KODADEK, T
BRAUMAN, JI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2588 - 2594
[10] COLLMAN JP, 1985, J AM CHEM SOC, V107, P4343

← 1 2 3 4 5 6 7 8 →