PERACID INDUCED RING-OPENING OF ISOXAZOLIDINES - A MECHANISTIC STUDY

被引：29

作者：

ALI, SA

WAZEER, MIM

机构：

[1] Chemistry Department, King Fahd University of petroleum and Minerals, Dhahran

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(00)79856-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformational analysis and mechanistic study of peracid induced ring opening of several isoxazolidines have been carried out. The orientation of the nitrogen lone pair dictates the regiochemistry of the ring opening which involves an intramolecular kinetic deprotonation of a nitroxonium ion intermediate.

引用

页码：3219 / 3222

页数：4

共 13 条

[1] ALI SA, 1988, TETRAHEDRON, V44, P5911
[2] ALI SA, 1990, TETRAHEDRON, V46, P7207
[3] THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF 1,3-DIPOLAR CYCLO-ADDITION OF A CYCLIC NITRONE
ALI, SA
WAZEER, MIM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03): : 597 - 605
[4] CYCLO-ADDITION OF 2,3,4,5-TETRAHYDROPYRIDINE N-OXIDE TO ISOBUTYL VINYL ETHER AND ALLYL ALCOHOL - METHYL 2-FORMYLMETHYLPIPERIDINE-1-CARBOXYLATE
CARRUTHERS, W
MOSES, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08): : 2251 - 2253
[5] Confalone P. N., 1988, ORG REACTIONS, V36, P1
[6] ELIEL EL, 1966, CONFORMATIONAL ANAL, P28
[7] HOOTELE C, 1987, B SOC CHIM BELG, V96, P57
[8] Ida H., 1983, YUKI GOSEI KAGAKU KY, V41, P652
[9] LABEL NA, 1964, J ORG CHEM, V29, P1337
[10] OXIDATION OF ISOXAZOLIDINES WITH PEROXY ACIDS - NITRONES AND N-HYDROXY-1,3-TETRAHYDROOXAZINES
LEBEL, NA
POST, ME
HWANG, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) : 1819 - 1823

← 1 2 →