Oxidative rearrangement of tertiary propargylic alcohols

Rodríguez, Arantxa; Moran, Wesley J.

Abstract

An oxidative rearrangement of tertiary alcohols mediated by m-CPBA is described that generates tetrasubstituted alkenes with a carboxylic acid substituent. The mechanism of the reaction is proposed to proceed through epoxidation of the alkyne to form an oxirene that undergoes a 1,2-aryl shift.

Citation

Rodríguez, A., & Moran, W. J. (2013). Oxidative rearrangement of tertiary propargylic alcohols. SYNLETT, 24(1), 102-104. https://doi.org/10.1055/s-0032-1317711

• Journal Article Type: Article
• Acceptance Date: Nov 7, 2012
• Online Publication Date: Dec 4, 2012
• Publication Date: 2013
• Deposit Date: May 22, 2024
• Journal: Synlett
• Print ISSN: 0936-5214
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 1
• Pages: 102-104
• DOI: https://doi.org/10.1055/s-0032-1317711
• Keywords: oxidation - rearrangement - propargylic alcohols - carboxylic acids - peroxy acid
• Public URL: https://keele-repository.worktribe.com/output/764022
• Publisher URL: https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0032-1317711