16504-87-3Relevant academic research and scientific papers
Exo- and Endohormones. XI. Synthesis of Monounsaturated Sex Pheromones of Lepitoptera via α-Dicetones
Oprean, I.,Ciupe, Hilke,Gansca, Lucia,Hodosan, F.
, p. 283 - 289 (2007/10/02)
α-Dicetones (5), prepared starting either with cyanohydrines (1) or with N,N-diethyl oxamate (6), were converted via the dihydrazones 11 ito acetylenes (12).Replacement of the protecting group by the acatate group and partial stereoselective reduction of the triple bond led finally to the title conpounds.
Vinylic Organoboranes. 3. Pheromones via Organoboranes. 1. Stereospecific Synthesis of Straight-Chain Z-Monoolefinic Insect Pheromones via Lithium (1-Alkynyl)trialkylborates
Brown, Herbert C.,Wang, Kung K.
, p. 4514 - 4517 (2007/10/02)
Various insect pheromones with straight-chain Z-monoolefinic structures have been prepared from lithium (1-alkynyl)trialkylborates.Treatment of lithium (1-alkynyl)trialkylborates, readily prepared from lithium acetylides and trialkylboranes, with iodine under mild conditions produces the corresponding alkynes in essentially quantitative yield.Monohydroboration of the resultant alkyne with 9-borabicyclononane yields the corresponding (Z)-olefin after protonolysis.The combination of these two reaction sequences provides a general route for the synthesis of (Z)-olefins.The position of the double bond and the carbon-chain length are easily controlled by properly choosing the initial reactants.The incorporation of functional groups is also easily achieved because of the mild reaction conditions and the tolerance of hydroboration to many functional groups.High yield and purity of the products are obtained.
