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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Crop Bioprotection Research » Research » Publications at this Location » Publication #101043
Title: IMPROVED HORNER-WADSWORTH-EMMONS OLEFINATION OF ALDEHYDES

Author
item Petroski, Richard

Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 8/26/1999
Publication Date: N/A
Citation: N/A

Interpretive Summary:

Technical Abstract: The E-isomer selectivity of the Horner-Wadsworth-Emmons olefination of aldehydes has been improved by using Lithium tert- butoxide as the base, triethyl-2-phosphonopropionate or triethyl- 2-phosphonobutyrate as the phosphonate, and an aldehyde such as 2-methyl-2-pentenal, with hexane as the reaction solvent. Greater E-isomer selectivity was observed in the formation of 2- methyldienoates than 2-ethyldienoates. Application to the synthesis of sap-beetle aggregation pheromones will be discussed.