A DARZENS AZIRIDINE SYNTHESIS

被引：67

作者：

DEYRUP, JA

机构：

[1] Department of Chemistry, University of Florida, Gainesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 09期

关键词：

D O I：

10.1021/jo01261a052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure has been developed which allows successful extension of the Darzens synthesis to the preparation of aziridine esters and amides. The stereochemical course of the condensation yields the unexpected result of preferential formation of trans ester and cis-amide. The significance and a possible explanation of this result are discussed. The chemistry of these aziridines has been briefly investigated and found to be dominated by the ease with which these compounds form azomethine ylides. © 1969, American Chemical Society. All rights reserved.

引用

页码：2724 / &

共 19 条

[1] Bhacca N. S., 1964, APPLICATIONS NMR SPE, P115
[2] BHACCA NS, 1964, APPLICATIONS NMR SPE, P121
[3] BHACCA NS, 1964, APPLICATIONS NMR SPE, P110
[4] ULTRAVIOLET SPECTRA OF N-PHENYL-SUBSTITUTED CYCLIC IMINES
BOTTINI, AT
NASH, CP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) : 734 - &
[5] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
COREY, EJ
CHAYKOVSKY, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
[6] NUCLEOPHILIC DISPLACEMENTS ON 3-MEMBERED RINGS
DEYRUP, JA
GREENWAL.RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (20) : 4538 - &
[7] DEYRUP JA, 1966, TETRAHEDRON LETT, P5091
[8] HEINE HW, 1965, TETRAHEDRON LETT, P3123
[9] HOUSE HO, 1965, MODERN SYNTHETIC REA, P240
[10] STEREOSPECIFIC CONVERSION OF CIS-TRANS ISOMERIC AZIRIDINES TO OPEN-CHAIN AZOMETHINE YLIDES
HUISGEN, R
SCHEER, W
HUBER, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (07) : 1753 - &

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