REVERSAL OF REGIOCHEMISTRY IN THE SYNTHESIS OF ISOXAZOLES BY NITRILE OXIDE CYCLOADDITIONS

被引：37

作者：

EASTON, CJ

HUGHES, CM

TIEKINK, ERT

LUBIN, CE

SAVAGE, GP

SIMPSON, GW

机构：

[1] CSIRO,DIV CHEM & POLYMERS,CLAYTON,VIC 3169,AUSTRALIA

[2] UNIV ADELAIDE,DEPT CHEM,ADELAIDE,SA 5005,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)73248-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isoxazolines 2a, 2b and 8 obtained from nitrile oxide cycloadditions to cyclohex-2-enone 1a and its analogues 1b and 7 reacted with nickel peroxide to give the isoxazoles 3a, 3b and 9. In contrast, the corresponding 2-bromocyclohex-2-enones 4a, 4b and 10, prepared by bromination of the corresponding alkenes la, Ib and 7, underwent nitrile oxide cycloadditions to afford the regioisomeric isoxazoles 6a, 6b and 12, respectively.

引用

页码：3589 / 3592

页数：4

共 11 条

[1]

AKHREM A A, 1976, Tetrahedron Letters, V44, P3983

[2]

BIANCHI G, 1979, J CHEM RES-S, P311

[3] 2-ISOXAZOLINE DERIVATIVES .8. REACTION OF NITRILE OXIDES WITH TROPONE [J].