An unexpected 1,2-hydride shift in phosphoric acid-promoted cyclodimerization of styrene oxides under solvent-free conditions. A synthetic route towards 2,4-disubstituted 1,3-dioxolanes

被引：12

作者：

Mazimba, Ofentse ^{[1
]}

Majinda, Runner R. ^{[1
]}

Masesane, Ishmael B. ^{[1
]}

机构：

[1] Univ Botswana, Dept Chem, Gaborone, Botswana

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 43期

关键词：

AMINO EPOXIDES; ALCOHOLS; AMINOEPOXIDES;

D O I：

10.1016/j.tetlet.2009.08.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 1,2-hydride shift in the phosphoric acid-promoted cyclodimerization of styrene oxide and its chloro derivatives under solvent-free conditions leading to 2,4-disubstituted 1,3-dioxolanes is described. Methoxy substituents on the aromatic ring of the styrene oxide prevent the 1,2-hydride shift reaction leading to substituted 1,4-dioxanes. A possible mechanism for the formation of the 1,3-dioxolanes is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5927 / 5929

页数：3