929906-56-9

Upstream product

• 135218-48-3 (E)-(3-(allyloxy)hexa-1,5-dien-1-yl)benzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 79299-29-9 (E)-1-phenyl-1,5-hexadien-3-ol 
• 100-42-5 styrene 
• 105598-43-4 1,5-hexadien-3-yl allyl ether 

Downstream Products

• 149795-91-5 6-((E)-Styryl)-3,4-dihydro-2H-pyran 
• 124851-36-1 (E)-2-styryl-3,4-dihydro-2H-pyran 

Relevant academic research and scientific papers

Selective formation of dihydropyran derivatives by a tandem domino ring-closing metathesis/cross-metathesis

A ring-closing metathesis (RCM)/cross-metathesis (CM) domino reaction has been applied to esters and unsymmetrical ether prepared from 1,5-hexadien-3-ol. For the first time, dihydropyran derivatives have been obtained via a regioselective cyclization. Thi

Ruthenium Catalysts Supported by Amino-Substituted N-Heterocyclic Carbene Ligands for Olefin Metathesis of Challenging Substrates

N-Heterocyclic carbene (NHC) ligands IMes (Formula presented.) and IMes (Formula presented.) derived from the well-known IMes ligand by substituting the carbenic heterocycle with one and two dimethylamino groups, respectively, were employed for the synthesis of second-generation Grubbs- and Grubbs–Hoveyda-type ruthenium metathesis precatalysts. Whereas the stability of the complexes was found to depend on the degree of dimethylamino-substitution and on the type of complex, the backbone-substitution was shown to have a positive impact on their catalytic activity in ring-closing metathesis, with a more pronounced effect in the second-generation Grubbs-type series. The new complexes were successfully implemented in a number of challenging olefin metathesis reactions leading to the formation of tetra-substituted C=C double bonds and/or functionalized compounds.

Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence

A novel ruthenium-catalyzed tandem ring-closing metathesis (RCM) double-bond isomerization reaction is described in this paper. The utility of this method for the efficient syntheses of five-, six-, and seven-membered cyclic enol ethers is demonstrated. It relies on the conversion of a metathesis-active ruthenium carbene species to an isomerization-active ruthenium-hydride species in situ. This conversion is achieved by using various additives. Scope and limitations of the different protocols are discussed, and some mechanistic considerations based on 31P and 1H NMR spectroscopic studies are presented.

In situ conversion of a Ru metathesis catalyst to an isomerization catalyst

Addition of alcohols and substoichiometric amounts of a base to a metathesis reaction induces conversion of the metathesis-active carbene catalyst to an isomerization-active hydride species.

An olefin metathesis/double bond isomerization sequence catalyzed by an in situ generated ruthenium hydride species

The direct conversion of allyl ethers to cyclic enol ethers using an olefin metathesis/double bond migration sequence is described. Ruthenium carbene complexes were activated to catalyze the double bond migration step by addition of hydride sources, such