Hydrido-Rhodium(I) and -Iridium(I) complex promoted ring-opening isomerization of unsymmetrically substituted methylenecyclopropanes into 1,3-dienes. Structures of intermediates and reaction pathways

被引：39

作者：

Nishihara, Y ^{[1
]}

Yoda, C ^{[1
]}

Osakada, K ^{[1
]}

机构：

[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan

来源：

ORGANOMETALLICS | 2001年 / 20卷 / 11期

关键词：

D O I：

10.1021/om010081n

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

2-Phenyl-1-methylenecyclopropane and 2,2-diphenyl-1-methylenecyclopropane react with MH(CO)(PPh3)(3) (M = Rh, Ir) to produce 1,3-dienes or the intermediate Rh and Ir complexes having a 3-butenyl ligand, depending on the conditions. The structures and chemical properties of the obtained complexes suggest plausible pathways for the ring-opening isomerization of the methylenecyclopropanes to the corresponding dienes.

引用

页码：2124 / 2126

页数：3

共 20 条

[1]

ALKIANIEC B, 1994, J AM CHEM SOC, V116, P9963

[2] RING STRAIN-ENERGY AND INVERSION BARRIER OF PHOSPHA[3]RADIALENE AND AZA[3]RADIALENE [J].

BACHRACH, SM .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (19) :4996-5000

[3] Synthesis of mono-, di-, and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanes catalyzed by Rh(I) complexes [J].

Bessmertnykh, AG ;

Blinov, KA ;

Grishin, YK ;

Donskaya, NA ;

Tveritinova, EV ;

Yureva, NM ;

Beletskaya, IP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6069-6076

[4]

BESSMERTNYKH AG, 1969, RUSS J ORG CHEM+, V34, P799

[5] STRUCTURAL CHARACTERIZATION IN SOLUTION OF INTERMEDIATES IN RHODIUM-CATALYZED HYDROFORMYLATION AND THEIR INTERCONVERSION PATHWAYS [J].

BROWN, JM ;

KENT, AG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (11) :1597-1607

[6] SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF THE D(0) TRANSITION METAL-ALKYL-ALKENE COMPLEX CP-ASTERISK-2YCH2CH2C(CH3)(2)CH=CH2 [J].

CASEY, CP ;

HALLENBECK, SL ;

POLLOCK, DW ;

LANDIS, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (38) :9770-9771

[7] RHODIUM-CATALYZED C-C COUPLING REACTIONS INVOLVING RING-OPENING OF STRAINED MOLECULES .2. ADDITION TO OLEFINS AND AROMATIC-SUBSTITUTION [J].

CHIUSOLI, GP ;

COSTA, M ;

MELLI, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 358 (1-3) :495-505

[8] KINETICS AND CONFORMATION IN THE REVERSIBLE INSERTION OF AN ALKENE INTO A PLATINUM CARBON BOND IN A CHELATED (PENTENYL)PLATINUM COMPLEX [J].

ERMER, SP ;

STRUCK, GE ;

BITLER, SP ;

RICHARDS, R ;

BAU, R ;

FLOOD, TC .

ORGANOMETALLICS, 1993, 12 (07) :2634-2643

[9] REVERSIBLE FORMAL ALKENE INSERTION INTO A CHELATED PLATINUM ALKYL BOND [J].

FLOOD, TC ;

BITLER, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6076-6077

[10] SYNTHESIS, CHARACTERIZATION, AND REARRANGEMENTS OF [(1-METHYLCYCLOBUTYL)METHYL]PLATINUM(II) COMPLEXES - VERY MILD RING-STRAIN-INDUCED CARBON CARBON ACTIVATION [J].

FLOOD, TC ;

STATLER, JA .

ORGANOMETALLICS, 1984, 3 (12) :1795-1803

← 1 2 →