OXYGEN EFFECT IN THE IODO LACTONIZATION OF UNSATURATED CARBOXYLIC-ACIDS LEADING TO 7-MEMBERED TO 12-MEMBERED RING LACTONES

被引：51

作者：

SIMONOT, B ^{[1
]}

ROUSSEAU, G ^{[1
]}

机构：

[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,CARBOCYCLES LAB,CNRS,URA 478,F-91405 ORSAY,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期

关键词：

D O I：

10.1021/jo00099a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of omega-alkenoic acids with bis(sym-collidine)iodine(I) hexafluorophosphate led to (iodomethyl) epsilon-caprolactones in good yields (49-75%) and medium ring iodo lactones in low yields (4-5%). The latter compounds have been obtained after introduction of an oxygen atom in the carbon chain. The position of the oxygen appeared important. This oxygen effect was explained by the stabilization of the intermediate iodonium ion by the oxygen atom.

引用

页码：5912 / 5919

页数：8

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