135583-04-9Relevant academic research and scientific papers
New and Convenient Synthesis of (Z)-Heneicos-6-en-11-one, the Douglas Fir Tussock Moth (Orgyia pseudotsugata) Sex Pheromone, and (Z)-Non-6-en-2-one, the Immediate Precursor for the Synthesis of Brevicomin, the Sex Attractant of the Western Pine Beetle Dentroctonus brevicomis
Ballini, Roberto
, p. 1419 - 1421 (2007/10/02)
Convenient syntheses of (Z)-heneicos-6-en-11-one and (Z)-non-6-en-2-one were achieved from (Z)-1-nitrodec-4-ene and (Z)-1-nitrohept-4-ene.Solvent-free nitroaldol reaction of (Z)-1-nitro-alkenes 1 with the aldehydes 2 on Amberlyst A-21, followed by in situ oxidation, gave the α-nitro ketones 3.Denitration via p-tolylsulphonylhydrazones and removal of the protecting group gave the title compounds 6a and 6b in 60 and 53 percent overall yield.
