Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles

被引：11

作者：

Baranac-Stojanovic, Marija ^{[1
,2
]}

Tatar, Jovana ^{[2
]}

Stojanovic, Milovan ^{[2
]}

Markovic, Rade ^{[1
,2
]}

机构：

[1] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia

[2] Ctr Chem ICTM, Belgrade 11000, Serbia

来源：

TETRAHEDRON | 2010年 / 66卷 / 34期

关键词：

4-Oxothiazolidine; Vinyl bromide; Bromophilic reaction; Carbanion; Rearrangement; HALOGEN MIGRATION; HALOPHILIC REACTIONS; SINGLE-STEP; SUBSTITUTION; DEBROMINATION; MECHANISMS; PERHALOFLUOROALKANES; REGIOSELECTIVITY; ISOMERIZATION; REARRANGEMENT;

D O I：

10.1016/j.tet.2010.06.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph3P, AcS-, CN-, I-, F-, Ac2CH- and N-3(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et3N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6873 / 6884

页数：12

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