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
收藏
页码：2355 / 2359
页数：5
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