Aromatic claisen rearrangements of benzyl ketene acetals: conversion of benzylic alcohols to (ortho-tolyl)acetates

Burns, Jed M., Krenske, Elizabeth H. and McGeary, Ross P. (2017) Aromatic claisen rearrangements of benzyl ketene acetals: conversion of benzylic alcohols to (ortho-tolyl)acetates. European Journal of Organic Chemistry, 2017 2: 252-256. doi:10.1002/ejoc.201601354


Author Burns, Jed M.
Krenske, Elizabeth H.
McGeary, Ross P.
Title Aromatic claisen rearrangements of benzyl ketene acetals: conversion of benzylic alcohols to (ortho-tolyl)acetates
Formatted title
Aromatic claisen rearrangements of benzyl ketene acetals: conversion of benzylic alcohols to (ortho-tolyl)acetates
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1099-0690
1434-193X
Publication date 2017-01-10
Sub-type Letter to editor, brief commentary or brief communication
DOI 10.1002/ejoc.201601354
Open Access Status Not yet assessed
Volume 2017
Issue 2
Start page 252
End page 256
Total pages 5
Place of publication London, United Kingdom
Publisher BioMed Central
Language eng
Abstract Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one-pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α-alkoxy substituent on the vinyl group. A [3,3]-sigmatropic mechanism was supported by trapping of the intermediate isotoluene in an intramolecular Alder–ene reaction.
Keyword Benzyl alcohols
Density functional calculations
Ketene acetals
Pericyclic reactions
Sigmatropic rearrangement
Q-Index Code CX
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Letter to editor, brief commentary or brief communication
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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