16695-41-3Relevant articles and documents
Libraries via Metathesis of Internal Olefins
Braendli, Christof,Ward, Thomas R.
, p. 1616 - 1621 (1998)
The cross-metathesis of internal olefins is applied for the combinatorial synthesis of small organic molecules; this reaction is conveniently carried out in neat olefin (oleic-acid derivatives) and requires only 0.001 equiv. of [Ru(CHPh)Cl2(PCy3)2] as catalyst (Cy = cyclohexyl).
Metathesis of Functionalized Alkenes. Synthesis of Insect Pheromones
Crisp, Geoffrey T.,Collis, Maree P.
, p. 935 - 942 (2007/10/02)
The ability of substituted phenoxy complexes of tungsten to effect metathesis of both functionalized and non-functionalized terminal alkenes has been investigated.This methodology has been applied to the synthesis of the insect pheromones tetradec-9-en-1-yl acetate, dodec-7-en-1-yl acetate and tricos-9-ene.
A General Approach to the Synthesis of Mono-olefinic Insect Sex Pheromones of Z- or E-Configuration
Fiandanese, Vito,Marchese, Giuseppe,Naso, Francesco,Ronzini, Ludovico
, p. 1115 - 1120 (2007/10/02)
A series of insect sex pheromones and structually related olefins have been synthesized with high stereoisomeric purity by two sequential cross-coupling reactions.Starting with (Z)- or (E)-1-bromo-2-phenylthioethene, (1) and (2), and Grignard reagents in the presence of nickel or palladium catalysts, two types of compounds have been prepared: (i) 1,2-dialkylethenes and (ii) alkenyl acetates.In the synthesis of Z-isomers, the first step involves a cross-coupling reaction of compound (1) with the appropriate Grignard reagent in the presence of a catalytic amount of .The second cross-coupling reaction is performed on the intermediate (Z)-phenylthioalkenes using a different Grignard reagent in the presence of (dppe=Ph2PCH2CH2PPh2) as a catalyst.In the synthesis of E-isomers both steps are cross-coupling reactions of Grignard reagents in the presence of as a catalyst, the first step involving compound (2) and the second step involving the intermediate (E)-phenylthioalkenes obtained.The Grignard reagents used in the synthesis of the alkenyl acetates derive from protected ω-halohydrins.
α-Haloallyllithium Species. Coupling with Alkyl Bromides
Macdonald, Timothy L.,Narayanan, Amirthalingam B.,O'Dell, Dale E.
, p. 1504 - 1506 (2007/10/02)
The regiospecific α-alkylation of in situ generated α-chloroallyllithium species with primary alkyl bromides and the synthetic utility of the derived secondary allylic chloride intermediates are described.
