单芳基取代的亚甲基环丁烷和亚甲基环丙烷与1-羟基苯并三唑（HOBt）、1-羟基-7-氮杂苯并三唑（HOAt）及1-羟基琥珀酰亚胺（HOSu）的反应

Reactions of monoaryl-substituted methylenecyclobutanes and methylenecyclopropanes with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu).

作者信息

Jiang Min, Shi Min

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China.

出版信息

J Org Chem. 2009 Mar 20;74(6):2516-20. doi: 10.1021/jo9000299.

DOI:10.1021/jo9000299

PMID:19222218

Abstract

Monoaryl-substituted methylenecyclobutanes (MCBs) and methylenecyclopropanes (MCPs) react with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu) smoothly to produce the corresponding cyclobutylmethanone and cyclopropylmethanone derivatives 2, 4, and 5 via a cascade epoxidation and nucleophilic addition process or the corresponding epoxides 6 in moderate to good yields under mild conditions. A plausible mechanism has been proposed on the basis of the control experiments and the isolation of the reaction intermediates.

摘要

单芳基取代的亚甲基环丁烷（MCBs）和亚甲基环丙烷（MCPs）与1-羟基苯并三唑（HOBt）、1-羟基-7-氮杂苯并三唑（HOAt）和1-羟基琥珀酰亚胺（HOSu）顺利反应，通过级联环氧化和亲核加成过程生成相应的环丁基甲酮和环丙基甲酮衍生物2、4和5，或者在温和条件下以中等至良好的产率生成相应的环氧化物6。基于对照实验和反应中间体的分离，提出了一种合理的反应机理。