THE INFLUENCE OF SUBSTITUENTS ON THE PHOTOCHEMICAL GENERATION AND STABILITY OF 2-MORPHOLINOCYCLOPROPANOLS

被引：9

作者：

WEIGEL, W

SCHILLER, S

RECK, G

HENNING, HG

机构：

[1] HUMBOLDT UNIV BERLIN,DEPT ORGAN & BIOORGAN CHEM,HESS STR 1-2,D-10115 BERLIN,GERMANY

[2] FED INST MAT RES & TESTING,D-12484 BERLIN,GERMANY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)61688-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By irradiation in oxygen-free ether alpha- or beta-substituted beta-morpholinopropiophenones 1a-c form the corresponding cyclopropanols 2 with 1-aryl and 2-morpholino group in a relative cis-configuration in high yields. The photocyclization of pure 1a-c enantiomers proceeds enantioselectively under these conditions. In methanol and presence of oxygen electronically excited 1c-h are converted to enaminones 3c-h via oxidation of intermediate cyclopropanols 2c-h. In the presence of electron-acceptor molecules this reaction apparently follows a SET mechanism.

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页码：6737 / 6740

页数：4

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