Synthetically useful Wagner-Meerwein rearrangement of α-quaternary β-bromovinyl methyl ethers

Ai Xia Wang; Yong Qiang Tu; Zhen Lei Song; Dao Yi Yuan; Xiang Dong Hu; Shao Hua Wang; Shuan Hu Gao

doi:10.1002/ejoc.200600195

Synthetically useful Wagner-Meerwein rearrangement of α-quaternary β-bromovinyl methyl ethers

Ai Xia Wang, Yong Qiang Tu^*, Zhen Lei Song, Dao Yi Yuan, Xiang Dong Hu, Shao Hua Wang, Shuan Hu Gao

^*Corresponding author for this work

Lanzhou University

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A synthetically useful Wagner-Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α-quaternary β-bromovinyl methyl ethers as well as the reaction conditions. γ-Aryl α,β-unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel-Crafts alkylation.

Original language	English
Pages (from-to)	2691-2694
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.200600195
State	Published - 12 Jun 2006
Externally published	Yes

Keywords

Lewis acids
Tricyclic systems
Unsaturated aldehydes
Vinyl methyl ethers
Wagner-Meerwein rearrangement

Access to Document

10.1002/ejoc.200600195

Cite this

@article{674e3b73d45546b2b98e5670dc678065,

title = "Synthetically useful Wagner-Meerwein rearrangement of α-quaternary β-bromovinyl methyl ethers",

abstract = "A synthetically useful Wagner-Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α-quaternary β-bromovinyl methyl ethers as well as the reaction conditions. γ-Aryl α,β-unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel-Crafts alkylation.",

keywords = "Lewis acids, Tricyclic systems, Unsaturated aldehydes, Vinyl methyl ethers, Wagner-Meerwein rearrangement",

author = "Wang, \{Ai Xia\} and Tu, \{Yong Qiang\} and Song, \{Zhen Lei\} and Yuan, \{Dao Yi\} and Hu, \{Xiang Dong\} and Wang, \{Shao Hua\} and Gao, \{Shuan Hu\}",

year = "2006",

month = jun,

day = "12",

doi = "10.1002/ejoc.200600195",

language = "英语",

pages = "2691--2694",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "12",

}

TY - JOUR

T1 - Synthetically useful Wagner-Meerwein rearrangement of α-quaternary β-bromovinyl methyl ethers

AU - Wang, Ai Xia

AU - Tu, Yong Qiang

AU - Song, Zhen Lei

AU - Yuan, Dao Yi

AU - Hu, Xiang Dong

AU - Wang, Shao Hua

AU - Gao, Shuan Hu

PY - 2006/6/12

Y1 - 2006/6/12

N2 - A synthetically useful Wagner-Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α-quaternary β-bromovinyl methyl ethers as well as the reaction conditions. γ-Aryl α,β-unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel-Crafts alkylation.

AB - A synthetically useful Wagner-Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α-quaternary β-bromovinyl methyl ethers as well as the reaction conditions. γ-Aryl α,β-unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel-Crafts alkylation.

KW - Lewis acids

KW - Tricyclic systems

KW - Unsaturated aldehydes

KW - Vinyl methyl ethers

KW - Wagner-Meerwein rearrangement

UR - https://www.scopus.com/pages/publications/33745672791

U2 - 10.1002/ejoc.200600195

DO - 10.1002/ejoc.200600195

M3 - 文章

AN - SCOPUS:33745672791

SN - 1434-193X

SP - 2691

EP - 2694

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

Synthetically useful Wagner-Meerwein rearrangement of α-quaternary β-bromovinyl methyl ethers

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this