REGIOSELECTIVE AND FACE-SELECTIVE CYCLOADDITION OF BENZONITRILE OXIDE AND C,N-DIPHENYLNITRONE TO 6,8-DIOXABICYCLO[3.2.1]OCT-3-ENE

被引：5

作者：

BLAKE, AJ ^{[1
]}

DAWSON, IM ^{[1
]}

FORSYTH, AC ^{[1
]}

GOULD, RO ^{[1
]}

PATON, RM ^{[1
]}

TAYLOR, D ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 01期

关键词：

D O I：

10.1039/p19930000075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzonitrile oxide, generated by dehydrochlorination of benzohydroximoyl chloride, undergoes regio-and face-selective cycloaddition to 6,8-dioxabicyclo[3.2.1]oct-3-ene 5 yielding a 4:1 mixture of 4,5-dihydroisoxazoles 6 and 7. Both products have exo-stereochemistry resulting from approach of the nitrile oxide from the face opposite the methyleneoxy bridge. The structures of the adducts were determined by H-1 NMR spectroscopy and, in the case of compound 6, by X-ray crystallography. The corresponding reaction with CN-diphenylnitrone yielded three of the eight possible isoxazolidines, the major isomer being exo,endo-adduct 16.

引用

页码：75 / 79

页数：5

共 17 条

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