SOLUTION PHOTOLYSIS OF CIS- AND TRANS-2-METHYLCYCLOPROPYL METHYL KETONE

被引：42

作者：

DAUBEN, WG

SCHUTTE, L

WOLF, RE

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 06期

关键词：

D O I：

10.1021/jo01258a069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photolysis of cis- (1) and trans-2-methylcyclopropyl methyl ketone (2) was studied in pentane and isopropyl alcohol. Irradiation of cis ketone 1 in either solvent yielded, exclusively, l-hexen-5-one (3). trans ketone 2 slowly formed 3 in pentane, presumably through isomerization to 1, but in addition gave two saturated ketones, n-butyl methyl ketone (4) and isobutyl methyl ketone (5). The formation of 4 and S occurs via opening of either of the cyclopropane bonds α to the carbonyl group, followed by hydrogen abstraction from the solvent. These results show that when an intramolecular y hydrogen abstraction (Norrish “type II”) can occur, this process will prevail over any other type of hydrogen migration. In addition, the efficiency of isopropyl alcohol to trap the intermediate radicals is demonstrated. © 1969, American Chemical Society. All rights reserved.

引用

页码：1849 / &

共 17 条

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