Reactions of Tricyclo[4.1.0.02,7]heptane and 1-Methyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide

被引：0

作者：

Kostryukov, S. G. ^{[1
]}

Masterova, Yu. Yu. ^{[1
]}

机构：

[1] Ogarev Mordovia State Univ, Saransk 430005, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 06期

关键词：

2-bromoethanesulfonyl bromide; tricyclo[4.1.0.0(2,7)]heptane; radical addition; bicyclo[3.1.1]heptane; dehydrobromination; ALPHA-HALOALKANESULFONYL BROMIDES; ORGANIC-SYNTHESIS; DERIVATIVES;

D O I：

10.1134/S1070428020060081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.0(2,7)]heptane and 1-methyltricyclo[4.1.0.0(2,7)]heptane according to a radical mechanism to give products of bothantiandsynaddition across the C-1-C(7)central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.

引用

页码：1014 / 1022

页数：9

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