39487-08-6Relevant academic research and scientific papers
The synthesis of long chain dialkylalkynes, dialkyldiynes and their hydrogenation to monoenes and dienes
Fisher,Tyman
, p. 1323 - 1338 (2007/10/03)
Long methylenic chain dialkylalkynes have been synthesised in high yield by an improved procedure. The methodology has been extended to nonconjugated diynes. Catalytic hydrogenation with a poisoned palladium catalyst affords cis-monoenes and cis, cis-dienes respectively. An improved synthesis of cis- 9-tricosene is described.
Vinylic Organoboranes. 5. An Improved, Convenient Synthesis of Unsymmetrical Alkynes via Iodination of Lithium Alkynyl "Ate" Complexes of Thexylalkylborinates
Sikorski, James A.,Bhat, N. G.,Cole, Thomas E.,Wang, Kung K.,Brown, Herbert C.
, p. 4521 - 4525 (2007/10/02)
The transfer reaction induced by iodination of lithium alkynyl "ate" complexes of organoboranes represents a novel route to unsymmetrical alkynes.Several potential "blocking" groups were examined in order to achieve the selective migration of one primary alkyl group and thereby increase the efficiency of this process.Best results were obtained with the combined use of the thexyl and methoxy moieties as "blocking" groups in this reaction.The required thexylalkylborinate intermediates were conveniently prepared in high yield from thexylchloroborane via hydroboration and methanolysis.Subsequent complexation with an appropriate lithium alkyne, followed by iodination, produced the desired unsymmetrical alkyne in high yield.Minimum amounts of the product resulting from competitive migration of the thexyl group were observed.Under these conditions, an efficient utilization of a primary alkyl group in this transfer reaction is achieved.Furthermore, the high tolerance of thexylchloroborane toward many functional groups and its high regioselectivity in terminal alkene hydroboration produces intermediates that are particularly useful for the synthesis of insect pheromones and not readily accessible via conventional organometallic procedures.
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.
INSECT PHEROMONES AND THEIR ANALOGS. XIV. SYNTHESIS OF MUSCALURE - THE SEX PHEROMONE OF Musca domestica
Odinokov, V. N.,Ishmuratov, G. Yu.,Balezina, G. G.,Bakhitov, R. Sh.,Tolstikov, G. A.
, p. 375 - 377 (2007/10/02)
A new route to the synthesis of tricos-9Z-one - the sex pheromone of the house fly - has been developed.
