Chemo-, regio-, and stereoselectivity in acid-catalyzed hydromethoxylation of tricyclo[4.1.0.02,7]hept-1-yl and 7-methyltricyclo[4.1.0.02,7]hept-1-yl phenyl sulfones

被引：0

作者：

V. A. Vasin

P. S. Petrov

V. A. Kalyazin

V. V. Razin

机构：

[1] Ogarev Mordovian State University,

[2] St. Petersburg State University,undefined

来源：

Russian Journal of Organic Chemistry | 2010年 / 46卷

关键词：

Heptane; Anhydrous Methanol; Cycloheptene; Sodium Hydrogen Carbonate; Anhydrous Sodium Carbonate;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Hydromethoxylation of tricyclo[4.1.0.02,7]hept-1-yl and 7-methyltricyclo[4.1.0.02,7]hept-1-yl phenyl sulfones with methanol at 20°C in the presence of a catalytic amount of perchloric acid is initiated by the endo attack of proton at the C1 atom, and the subsequent cleavage of the side C1–C2 bond leads to formation of mixtures of diastereoisomeric exo-7-phenylsulfonyl-2-methoxybicyclo[4.1.0]heptanes, the endo-2 isomer prevailing. Probable factors responsible for the observed chemo-, regio-, and stereoselectivity of the addition are discussed.

引用

页码：812 / 819

页数：7

共 68 条

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