ORGANIC-SYNTHESIS UTILIZING BECKMANN FRAGMENTATION - NEW CARBON CARBON BOND FORMATION BY THE REACTION OF ALPHA-ALKOXYCYCLOALKANONE OXIME ACETATES WITH ORGANOALUMINUM REAGENTS

被引：13

作者：

FUJIOKA, H

YAMANAKA, T

TAKUMA, K

MIYAZAKI, M

KITA, Y

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 07期

关键词：

D O I：

10.1039/c39910000533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of alpha-alkoxycycloalkanone oxime acetates 1 with organoaluminium reagents caused Beckmann fragmentation and subsequent carbon-carbon bond formation to give various types of omega-cyano-alpha-alkyl (or alkynyl)ethers 2 in high yields.

引用

页码：533 / 534

页数：2

共 8 条

[1] BECKMANN FRAGMENTATION AND SUCCESSIVE CARBON-CARBON BOND FORMATION OF ALPHA-ALKOXYCYCLOALKANONE OXIMES CATALYZED BY TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE [J].

FUJIOKA, H ;

MIYAZAKI, M ;

YAMANAKA, T ;

YAMAMOTO, H ;

KITA, Y .

TETRAHEDRON LETTERS, 1990, 31 (41) :5951-5954

[2]

GAWLEY RE, 1986, ORG REACTIONS, V35, P1

[3] MECHANISMS AND STEREOCHEMISTRY OF HETEROLYTIC FRAGMENTATION [J].

GROB, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :535-&

[4] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS [J].

GROB, CA ;

SCHIESS, PW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :1-&

[5]

Heldt W. Z., 1960, ORG REACTIONS, V11, P1

[6] ORGANOALUMINUM-PROMOTED BECKMANN REARRANGEMENT OF OXIME SULFONATES [J].

MARUOKA, K ;

MIYAZAKI, T ;

ANDO, M ;

MATSUMURA, Y ;

SAKANE, S ;

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2831-2843

[7]

MCCARTY CG, 1970, CHEM CARBON NITROGEN, P416

[8]

OHNO M, 1968, KAGAKU NO RYOIKI, V22, P30

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