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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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