Type 2 Ring-Opening Reactions of Cyclopropanated 7-Oxabenzonorbornadienes under Acid Catalysis

被引：9

作者：

Tigchelaar, Andrew ^{[1
]}

Haner, Jamie ^{[1
]}

Carlson, Emily ^{[1
]}

Tam, William ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

SYNLETT | 2014年 / 25卷 / 16期

基金：

加拿大自然科学与工程研究理事会;

关键词：

fused-ring systems; cyclopropane; ring-opening reactions; regioselectivity; acid catalysis; OXABICYCLIC ALKENES; ORGANIC HALIDES; ACTIVATION; REDUCTION; MECHANISM; STRATEGY; SYSTEMS; SCOPE;

D O I：

10.1055/s-0034-1378581

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel ring-opening mode of cyclopropanated 7-oxabenzonorbornadiene under acid catalysis has been discovered, providing various 2-(alkoxymethyl)naphthalenes through the use of alcohol nucleophiles. The reaction was most effective with catalytic p-TsOH center dot H2O in methanol, offering yields up to 91%. The compatibility of secondary and tertiary alcohols, as well as functionalized substrates was also demonstrated.

引用

页码：2355 / 2359

页数：5

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