Influence of E/Z isomerism of aldoximes on the direction of their alkylation with oxirane

被引：4

作者：

Bakunova, SM ^{[1
]}

Grigor'ev, IA ^{[1
]}

Volodarsky, LB ^{[1
]}

机构：

[1] Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Branch, Novosibirsk 630090, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 1999年 / 48卷 / 07期

关键词：

oxirane; aldoximes; alpha-aryl-N-(2-hydroxyethyl)nitrons;

D O I：

10.1007/BF02495314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of Z-2-furaldoxime with oxirane afforded the N-alkylation product, viz., alpha-2-furyl-N-(2-hydroxyethyl)nitron, in good yield. E-Benzaldoxime gave predominantly the O-alkylation product, while its Z isomer was converted into a mixture with the N-alkylation product slightly predominating.

引用

页码：1389 / 1391

页数：3

共 8 条

[1] [Anonymous], 1984, SVOISTVA ORGANICHESK
[2] ALKYLATION OF NITROPARAFFINS AND OXIMES WITH EPOXIDES
BACHMAN, GB
HOKAMA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) : 4223 - 4225
[3] BJORGO J, 1974, J CHEM SOC CHEM COMM, P478
[4] ALKYLATION OF SYN- AND ANTI-BENZALDOXIMES
BUEHLER, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) : 261 - &
[5] TANDEM NUCLEOPHILIC SUBSTITUTION 1,3 DIPOLAR CYCLO-ADDITION REACTIONS OF OXIMES WITH EPOXIDES AND DIPOLAROPHILES
GRIGG, R
MARKANDU, J
[J]. TETRAHEDRON LETTERS, 1989, 30 (40) : 5489 - 5492
[6] RING-CHAIN ISOMERISM OF N-(2-HYDROXYALKYL)NITRONES .1. NITRONES OF SUBSTITUTED BENZALDEHYDES
KLIEGEL, W
BECKER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (06): : 2067 - 2089
[7] KLIEGEL W, 1970, LIEBIGS ANN CHEM, V733, P192
[8] SYNTHESIS AND SEPARATION OF THE E-ISOMER AND Z-ISOMER OF SIMPLE ALDONITRONES
SIVASUBRAMANIAN, S
MOHAN, P
THIRUMALAIKUMAR, M
MUTHUSUBRAMANIAN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23): : 3353 - 3354

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