Nitrochlorination of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone

被引：0
|
作者：
V. A. Vasin
S. G. Kostryukov
A. V. Semenov
V. V. Razin
机构：
[1] Ogarev Mordovian State University,
[2] St. Petersburg State University,undefined
来源：
Russian Journal of Organic Chemistry | 2008年 / 44卷
关键词：
Diethyl Ether; Sodium Hydrogen Carbonate; Phenyl Sulfone; Anhydrous Chloroform; NOCl;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Treatment of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone with a ∼1:8 mixture of N2O4 and NOCl in diethyl ether at −5 to 0°C gave products of formal anti-addition of NO2Cl at the central C1-C7 bond. In the reaction with phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone nitryl chloride acts as an effective chlorinating agent; as a result, a mixture of diastereoisomeric syn- and anti-6,7-dichlorobicyclo[3.1.1]hept-6-yl phenyl sulfones at a ratio of 7.5:1 is formed.
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页码：528 / 531
页数：3
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