Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg(OAc)<inf>2</inf>

Sastraruji, T; Pyne, SG; Ung, AT

Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg(OAc)<inf>2</inf>

Sastraruji, T Pyne, SG Ung, AT

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Publication Type:: Journal Article
Citation:: Tetrahedron, 2012, 68 (2), pp. 598 - 602
Issue Date:: 2012-01-14

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Field	Value	Language
dc.contributor.author	Sastraruji, T	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.date.issued	2012-01-14	en_US
dc.identifier.citation	Tetrahedron, 2012, 68 (2), pp. 598 - 602	en_US
dc.identifier.issn	0040-4020	en_US
dc.identifier.uri	http://hdl.handle.net/10453/18050
dc.description.abstract	Oxidation of (11Z)-1′,2′-didehydrostemofoline with DIB/TBHP/Mg(OAc)2·4H2O resulted in oxidative cleavage of the C-11-C-12 double bond instead of the desired allylic oxidation of the 1-butenyl side chain. Stemofoline gave a similar result. The oxidation of more simple terminal alkenes was regioselective and gave vinyl ketones while allyl and benzyl ethers gave acrylate and benzoate esters, respectively. Allyl and benzyl ethers could be chemoselectively oxidized in the presence of a terminal alkene or benzyl group. Oxidation of an internal alkene was poorly regioselective, in contrast to the oxidation of 1-substituted cyclohexenes. © 2011 Elsevier Ltd. All rights reserved.	en_US
dc.relation.ispartof	Tetrahedron	en_US
dc.relation.isbasedon	10.1016/j.tet.2011.10.112	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg(OAc)<inf>2</inf>	en_US
dc.type	Journal Article
utslib.citation.volume	2	en_US
utslib.citation.volume	68	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	open_access
pubs.issue	2	en_US
pubs.publication-status	Published	en_US
pubs.volume	68	en_US

Abstract:

Oxidation of (11Z)-1′,2′-didehydrostemofoline with DIB/TBHP/Mg(OAc)2·4H2O resulted in oxidative cleavage of the C-11-C-12 double bond instead of the desired allylic oxidation of the 1-butenyl side chain. Stemofoline gave a similar result. The oxidation of more simple terminal alkenes was regioselective and gave vinyl ketones while allyl and benzyl ethers gave acrylate and benzoate esters, respectively. Allyl and benzyl ethers could be chemoselectively oxidized in the presence of a terminal alkene or benzyl group. Oxidation of an internal alkene was poorly regioselective, in contrast to the oxidation of 1-substituted cyclohexenes. © 2011 Elsevier Ltd. All rights reserved.

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http://hdl.handle.net/10453/18050