Ring-opening of epoxides promoted by organomolybdenum complexes of the type [η5-C5H4R)mo(CO)2(773-C3H5)] and [(η5-C5H5) Mo(CO)3(CH2R)]

被引：12

作者：

Bruno, Sofia M. ^{[1
]}

Gomes, Ana C. ^{[1
]}

Abrantes, Marta ^{[2
]}

Valente, Anabela A. ^{[1
]}

Pillinger, Martyn ^{[1
]}

Goncalves, Isabel S. ^{[1
]}

机构：

[1] Univ Aveiro, CICECO Aveiro Inst Mat, Dept Chem, P-3810193 Aveiro, Portugal

[2] Univ Lisbon, Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2015年 / 799-800卷

关键词：

Molybdenum carbonyl complexes; Acid catalysis; Epoxides; Ring-opening reactions; Isomerization; Alchoholysis; ALPHA-PINENE OXIDE; ACID CATALYST; LEWIS-ACIDS; ISOMERIZATION; MOLYBDENUM(II); ALCOHOLYSIS; CHEMISTRY;

D O I：

10.1016/j.jorganchem.2015.09.022

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cyclopentadienyl molybdenum carbonyl complexes [(775-05H(4)R)Mo(CO)(2)(773-C3H5) and [(eta(5)-C5H5) Mo(CO)(3)(CH2R)] (R = H, COOH) have been shown to promote acid-catalysed reactions in liquid phase, under moderate conditions. The catalytic alcoholysis of styrene oxide with ethanol at 35 degrees C gave 2ethoxy-2-phenylethanol in 100% yield within 30 min for the dicarbonyl complexes and 3-6 h for the tricarbonyl complexes. Steady catalytic performances were observed in consecutive runs with the same catalytic solution, suggesting fairly good catalytic stability. In the second acid-catalysed reaction studied, the isomerization of a-pinene oxide at 55 degrees C gave campholenic aldehyde and trans-carveol in a total yield of up to 86% at 100% conversion. Chemoselectivity is shown to be solvent dependent. (C) 2015 Elsevier BY. All rights reserved.

引用

页码：179 / 183

页数：5

共 50 条

[1] Decamethylpentasilacycloheptyne • Mo2(CO)4(η5-C5H5)2 and cycloheptyne • Mo2(CO)4(η5-C5H5)2
Cervantes-Lee, F
Parkanyi, L
Kapoor, RN
Mayr, AJ
Pannell, KH
Pang, Y
Barton, TJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 562 (01) : 29 - 33
[2] Transition metal-substituted paraffins:: synthesis and properties of some μ-saturated heterobimetallic complexes containing Mo and W or Fe and the crystal structures of [(η5-C5H5)(CO)3W(CH2)3Mo(CO)2(PPh3)(η5-C5H5)] and [(η5-C5H5)(CO)2(PPh3)Mo(CH2)3Fe(CO)2(η5-C5H5)]
Friedrich, HB
Howie, RA
Laing, M
Onani, MO
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (01) : 181 - 193
[3] Synthesis and photolysis of [M(CO)3H]2(η5,η5-C5H4CH2C5H4), where M = Mo and W.: Photochemical 'twist' rearrangement of M2(CO)6 (η5,η5-C5H4CH2C5H4) to give [M(CO)3][M(CO)3H](η5,η5:η1-C5H4CH2C5H3), where M = Mo and W.: The molecular structure [Mo(CO)3][Mo(CO)3Cl](η5,η5:η1-C5H4CH2C5H3)
Bitterwolf, TE
Saygh, A
Haener, JL
Fierro, R
Shade, JE
Rheingold, AL
Liable-Sands, L
Alt, HG
[J]. INORGANICA CHIMICA ACTA, 2002, 334 : 54 - 58
[4] Synthesis and photochemistry of ring-coupled heterobimetallic compounds of ruthenium.: The molecular structures of RuM(CO)5(μ-η5,η5-C5H4CR2C5H4), where M = Mo, R = CH3;: M = W, R = H, [Ru(CO)2][Mo(CO)3Cl](μ-η5,η1:η5-C5H4CH2C5H3) and [W(CO)3][Ru(CO)2Cl](μ-η5,η1:η5-C5H4CH2C5H3)
Bitterwolf, TE
Saygh, AA
Shade, JE
Rheingold, AL
Yap, GPA
Lable-Sands, LM
[J]. INORGANICA CHIMICA ACTA, 2000, 300 : 800 - 809
[5] STRUCTURAL DETERMINATION OF [(C5H5)2MO(H)CO][(C5H5)MO(CO)3]
ADAMS, MA
FOLTING, K
HUFFMAN, JC
CAULTON, KG
[J]. INORGANIC CHEMISTRY, 1979, 18 (11) : 3020 - 3023
[6] Synthesis, Nujol matrix and solution photochemistry of M(CO)2[η5,η3-C5H4-C(CH3)2-C5H6] (where M = Cr or Mo):: molecular structures of Cr(CO)2[η5,η3-C5H4-C(CH3)2-C5H6], Mo(CO)2[η5,η3-C5H4-C(CH3)2-C5H6], and Mo(CO)[P(C6H5)3][η5,η3-C5H4-C(CH3)2-C5H6]
Bitterwolf, TE
Saygh, AA
Bays, JT
Weiss, CA
Scallorn, WB
Shade, JE
Rheingold, AL
Liable-Sands, L
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 583 (1-2) : 152 - 161
[7] DEOXYGENATIVE REDUCTION OF DIMOLYBDENUM CARBONYL-COMPLEXES MO-2(ETA(5)-C(5)H(4)R')(2)(CO)(4) BY HYDROSILANE GIVING TRINUCLEAR MU(3)-ETHYLIDYNE AND MU(3)-ETHYLIDYNE COMPLEXES, (MU(3)-CR)[MO(ETA(5)-C(5)H(4)R')(CO)(2)](3)(R,R'=H,CH3), AND ANALYSIS OF THE ROTATIONAL PROCESSES OF THE MO(ETA(5)-C(5)M(4)R')(CO)(2) MOIETIES
AKITA, M
NODA, K
TAKAHASHI, Y
MOROOKA, Y
[J]. ORGANOMETALLICS, 1995, 14 (11) : 5209 - 5220
[8] THE ELECTRONIC-STRUCTURES OF [(C5H4-C6H5)CR(CO)3]-, [(C6H4COC6H5)CR(CO)3)-, [(C5H4CH2C6H5)CR(CO)3]-, [(C5H4C2H2C6H5)CR(CO)3]- AND (C6H5-C5H4)MN(CO)3, (C6H5COC5H4)MN(CO)3, (C6H5CH2C5H4)MN(CO)3, (C6H5C2H2C5H4)MN(CO)3
FITZPATRICK, NJ
GOGAN, NJ
SAYAL, PK
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (02) : C31 - C34
[9] Rotameric transformations in the photochemistry of (η5-C5H5)Ru(CO)(η3-C3H5) and (η3-C3H4R)Fe(CO)2NO, where R = H or Me
Bitterwolf, TE
[J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2004, 7 (08) : 956 - 959
[10] HEATS OF REACTION OF HMO(CO)3C5H5, CH3MO(CO)3C5H5, C2H5MO(CO)3C5H5 WITH PHOSPHINES AND PHOSPHITES - THERMODYNAMIC STUDY OF THE COINSERTION REACTION
NOLAN, SP
DELAVEGA, RL
MUKERJEE, SL
HOFF, CD
[J]. INORGANIC CHEMISTRY, 1986, 25 (08) : 1160 - 1165

← 1 2 3 4 5 →