Reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone with dimethyl diazomalonate catalyzed by Rh2(OAc)4

被引：0
|
作者：
Mloston, G
Romanski, J
Heimgartner, H
机构：
[1] Univ Lodz, Sect Heteroorgan Cpds, PL-90136 Lodz, Poland
[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
来源：
POLISH JOURNAL OF CHEMISTRY | 2002年 / 76卷 / 04期
关键词：
carbenoids; 1,3-and 1,5-dipolar electrocyclization; 1,3-oxathioles; thiiranes; thiocarbonyl ylides;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with dimethyl diazomalonate ;in the presence of Rh-2(OAc)(4) in toluene at 50degreesC yielded a mixture of three products 10, 11, and 12. Thiocarbonyl ylide 8 is believed to be the common intermediate. The formation of 10 is rationalized by the 1,3-dipolar electrocyclization of 8 to give spirocyclic thiirane 9, which spontaneously eliminated sulfur. On the other hand, the 1,5-dipolar electrocyclization of 8 led to 1,3-oxathiole 11, which is converted into lactone 12 by hydrolysis.
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页码：551 / 555
页数：5
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