Oxidant effect, skeletal rearrangements and solvent interception in oxidative triflamidation of norbornene and 2,5-norbornadiene

被引：20

作者：

Moskalik, Mikhail Yu ^{[1
]}

Shainyan, Bagrat A. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Sterkhova, Irina, V ^{[1
]}

Astakhova, Vera V. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

来源：

TETRAHEDRON | 2020年 / 76卷 / 11期

关键词：

Oxidative triflamidation; Norbornene; Norbornadiene; Skeletal rearrangements; Oxidant effect; Heterocyclization; COPPER-CATALYZED AZIRIDINATION; ELECTROPHILIC DIAMINATION; HETEROCYCLIC-COMPOUNDS; OLEFINS; ALKENES; ARENESULFONAMIDES; HYDROAMINATION; SULFAMIDATION; SULFONAMIDES; FRAMEWORK;

D O I：

10.1016/j.tet.2020.131018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unlike the previous studies of oxidative triflamidation, the reactions of triflamide with norbornene and norbornadiene in nitrites RCN (R = Me, i-Bu, Ph) or THE in the presence of t-BuOI, NBS or NIS as oxidants proceed with skeletal rearrangements to give bicyclic and tricyclic products of triflamidation or halotriflamidation with incorporation of the solvent molecule fragments. The stereoselectivity of the reaction depends on the oxidant used - t-BuOI or NXS. (C) 2020 Published by Elsevier Ltd.

引用

页数：9

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