A CONVENIENT SYNTHESIS OF (E)-NON-3-ENE-2,5-DIONE, AN IMPORTANT COMPONENT ISOLATED FROM THE FIRE BEE TRIGONA-TATAIRA

Authors
BALLINI R ASTOLFI P
Citation
R. Ballini et P. Astolfi, A CONVENIENT SYNTHESIS OF (E)-NON-3-ENE-2,5-DIONE, AN IMPORTANT COMPONENT ISOLATED FROM THE FIRE BEE TRIGONA-TATAIRA, Liebigs Annalen, (11), 1996, pp. 1879-1880
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
11
Year of publication
1996
Pages
1879 - 1880
Database
ISI
SICI code
0947-3440(1996):11<1879:ACSO(A>2.0.ZU;2-7
Abstract
(E)-Non-3-ene-2,5-dione (5) the main component isolated from the volat ile compounds derived from the cephalic secretion of workers of Trigon a tataira, was conveniently prepared by nitroaldol reaction between pe ntanal 1 and 1-nitrobutan3-ol (rac-2) catalyzed by Amberlyst A-21. The resulting beta-nitro alcohol rac-3 was oxidized to the alpha-nitro ke tones 4, which via elimination of nitrous acid (Et(3)N), afforded the enedione 5 in good yield.