Reactions of a metallacyclobutene complex with alkenes

被引：19

作者：

Holland, Ryan L. ^{[1
]}

Bunker, Kevin D. ^{[1
]}

Chen, Christopher H. ^{[1
]}

DiPasquale, Antonio G. ^{[1
]}

Rheingold, Arnold L. ^{[1
]}

Baldridge, Kim K. ^{[2
]}

O'Connor, Joseph M. ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 31期

关键词：

D O I：

10.1021/ja803701z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first production reactions of a characterized metallacyclobutene complex with alkenes are reported. Thus, the metallcyclobutene complex (eta(5)-C5H5)(PPh3)Co[kappa(2)-(C,C)-C(SO2Ph)=C(Si(CH3)(3))CH(CO2CH2CH3)] (2) undergoes reaction with alkenes to give 1,4-diene complexes with a high degree of regio- and stereoselectivity. A mechanism is proposed in which the metallacyclobutene generates a cyclic vinylcarbene intermediate that undergoes [4+2]-cycloaddition reactions with activity quantum mechanical methods.

引用

页码：10093 / +

页数：4

共 27 条

[1] Envelope-flip dynamics in CpCo(diene) complexes: an ab initio quantum mechanical study [J].

Baldridge, KK ;

O'Connor, JM ;

Chen, MC ;

Siegel, JS .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (49) :10126-10131

[2] METALLABICYCLO(3.1.0)HEXENES AND THEIR REARRANGEMENT TO VINYLMETALLACYCLOBUTENES (M = TI, ZR) [J].

BINGER, P ;

MULLER, P ;

LANGHAUSER, F ;

SANDMEYER, F ;

PHILIPPS, P ;

GABOR, B ;

MYNOTT, R .

CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (07) :1541-1550

[3] Aromatic iridacycles [J].

Bleeke, John R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (10) :1035-1047

[4] Kinetic addition of nucleophiles to η3-propargyl rhenium complexes occurs at the central carbon to produce rhenacyclobutenes [J].

Casey, CP ;

Nash, JR ;

Yu, CS ;

Selmeczy, AD ;

Chung, S ;

Powell, DR ;

Hayashi, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :722-733

[5] Synthesis of metallacyclobutenes of late transition metals via nucleophilic addition of allenyl or propargyl complexes [J].

Cheng, YC ;

Chen, YK ;

Huang, TM ;

Yu, CI ;

Lee, GH ;

Wang, Y ;

Chen, JT .

ORGANOMETALLICS, 1998, 17 (14) :2953-2957

[6] REACTIONS OF COORDINATED LIGANDS .13. RING-OPENING OF 2,3-BIS-(HYDROXYMETHYL)METHYLENECYCLOPROPANE WITH NONACARBONYLDI-IRON - MOLECULAR AND CRYSTAL-STRUCTURES OF TRICARBONYL-ETA4-[3-METHYLENE-ENDO-4-VINYLDIHYDROFURAN-2(3H)-ONE]IRON(O] AND TETRACARBONYL-ETA2-[3-METHYL-ENE-EXO-4-VINYLDIHYDROFURAN-2(3H)-ONE]IRON(0)Y [J].

CHISNALL, BM ;

GREEN, M ;

HUGHES, RP ;

WELCH, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (19) :1899-1907

[7] Metal carbenes in enyne metathesis: Synthetic and mechanistic studies [J].

Diver, Steven T. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 254 (1-2) :29-42

[8]

DOXSEE KM, 1992, SYNLETT, P13

[9] 1ST PHOTOCHEMICAL ENVELOPE ISOMERIZATION OF A LATE-TRANSITION-METAL 1,3-BUTADIENE COMPLEX - A TRIPLE STEREOCHEMICAL LABELING EXPERIMENT [J].

EATON, B ;

KING, JA ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) :1359-1360

[10] Cobalt(I)-mediated preparation of polyborylated cyclohexadienes:: Scope, limitations, and mechanistic insight [J].

Geny, Anais ;

Leboeuf, David ;

Rouquie, Gabriel ;

Vollhardt, K. Peter C. ;

Malacria, Max ;

Gandon, Vincent ;

Aubert, Corinne .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (19) :5408-5425

← 1 2 3 →