Iron Lewis acid catalyzed reactions of phenyldiazomethane with aromatic aldehydes

被引：30

作者：

Mahmood, SJ ^{[1
]}

Saha, AK ^{[1
]}

Hossain, MM ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4020(97)10287-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iron Lewis acid 1 was found to catalyze reactions of phenyldiazomethane and aromatic aldehydes to give cisepoxides along with the corresponding ketones. The yield of the epoxide increased with electron-withdrawing substituents on the aldehyde, while little or no epoxide was formed with electron-donating substituents. The reaction was found to go through the coordination of the aldehyde to the iron Lewis acid instead of a carbene intermediate. (C) 1997 Elsevier Science Ltd. All rights reserved.

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页码：349 / 358

页数：10

相关论文

共 25 条

[1] NOVEL CATALYTIC CYCLE FOR THE SYNTHESIS OF EPOXIDES FROM ALDEHYDES AND SULFUR YLIDES MEDIATED BY CATALYTIC QUANTITIES OF SULFIDES AND RH-2(OAC)(4) [J].

AGGARWAL, VK ;

ABDELRAHMAN, H ;

JONES, RVH ;

LEE, HY ;

REID, BD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5973-5974

[2] SEMI-PINACOL REARRANGEMENTS INVOLVING TRIFLUOROMETHYLPHENYL GROUPS [J].

BLANCO, FE ;

HARRIS, FL .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) :868-871

[3] INVESTIGATION OF THE STEREOCHEMISTRY OF FE-C-ALPHA BOND-CLEAVAGE WHEN PHENYLCYCLOPROPANE IS GENERATED BY GAMMA-IONIZATION OF STEREOSPECIFICALLY DEUTERATED C5H5(CO)2FECHDCHDCH(OCH3)C6H5 COMPLEXES - A TRANSITION-STATE MODEL FOR TRANSFER OF THE CARBENE LIGAND FROM C5H5(CO)2FE = CHR+ TO ALKENES [J].

BROOKHART, M ;

LIU, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :939-944

[4]

CAREY FA, 1990, ADV ORGANIC CHEM A, P275

[5] STEREOCHEMISTRY AND MECHANISM OF CYCLOPROPANE FORMATION FROM IONIZATION OF C5H5(CO)2FE(CH2)3X [J].

CASEY, CP ;

VOSEJPKA, LJS .

ORGANOMETALLICS, 1992, 11 (02) :738-744

[6] IS PI-BACK-BONDING IMPORTANT FOR SIGMA-BOUND ALDEHYDE AND KETONE COMPLEXES - SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF AROMATIC ALDEHYDE COMPLEXES OF THE [CPFE(CO)(2)](+) CATION [J].

CICERO, RL ;

PROTASIEWICZ, JD .

ORGANOMETALLICS, 1995, 14 (10) :4792-4798

[7] DEVELOPMENTS IN CHEMISTRY OF DIAZO-ALKANES [J].

COWELL, GW ;

LEDWITH, A .

QUARTERLY REVIEWS, 1970, 24 (01) :119-&

[8]

Creary X, 1986, ORG SYNTH, V64, P207, DOI DOI 10.1021/J001285A059

[9]

GUTSCHE CD, 1954, ORG REACTIONS, V8, P365

[10]

Hegarty A. F., 1978, CHEM DIAZONIUM DIA 2, P511