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Use of the Anti-Oxidant Butylated Hydroxytoluene in situ for the Synthesis of Readily Oxidized Compounds: Application to the Synthesis of the Moth Pheromone (Z,Z,Z)-3,6,9-Nonadecatriene

Citation

Davies, NW and Meredith, GS and Molesworth, PP and Smith, JA, Use of the Anti-Oxidant Butylated Hydroxytoluene in situ for the Synthesis of Readily Oxidized Compounds: Application to the Synthesis of the Moth Pheromone (Z,Z,Z)-3,6,9-Nonadecatriene, Australian Journal of Chemistry, 60, (11) pp. 848-849. ISSN 0004-9425 (2007) [Refereed Article]

DOI: doi:10.1071/CH07223

Abstract

The triene (Z,Z,Z)-3,6,9-nonadecatriene was synthesized in three steps from methyl linolenate. The key to the synthesis was the use of the anti-oxidant butylated hydroxytoluene in situ to provide protection of the unstable triene from autoxidation during reaction workup. This simple modification resulted in an increase in the yield from 20 to 85% over three steps. © CSIRO 2007.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Davies, NW (Associate Professor Noel Davies)
Author:Meredith, GS (Mr Graham Meredith)
Author:Molesworth, PP (Dr Peter Molesworth)
Author:Smith, JA (Mr John Smith)
ID Code:51157
Year Published:2007
Web of Science® Times Cited:6
Deposited By:Chemistry
Deposited On:2007-08-01
Last Modified:2008-04-30
Downloads:0

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