Oxidative cleavage of allyl ethers by an oxoammonium salt

Christopher B Kelly; John M Ovian; Robin M Cywar; Taylor R Gosselin; Rebecca J Wiles; Nicholas E Leadbeater

doi:10.1039/c5ob00270b

Oxidative cleavage of allyl ethers by an oxoammonium salt

Org Biomol Chem. 2015 Apr 14;13(14):4255-9. doi: 10.1039/c5ob00270b. Epub 2015 Mar 6.

Authors

Christopher B Kelly¹, John M Ovian, Robin M Cywar, Taylor R Gosselin, Rebecca J Wiles, Nicholas E Leadbeater

Affiliation

¹ Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA. nicholas.leadbeater@uconn.edu.

PMID: 25748071
DOI: 10.1039/c5ob00270b

Abstract

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aldehydes / chemistry
Cyclic N-Oxides / chemistry*
Ethers / chemistry*
Ketones / chemistry
Oxidation-Reduction
Solvents / chemistry

Substances

Aldehydes
Cyclic N-Oxides
Ethers
Ketones
Solvents