68480-13-7

Upstream product

• 10339-62-5 (E)-4-decen-1-ol 
• 57074-37-0 (Z)-4-decen-1-ol 
• 30390-50-2 (Z)-4-decenal 

Downstream Products

• 67634-08-6 1-acetoxy-1-(2'-tetrahydrofuryl)hexane 

Relevant academic research and scientific papers

An effective procedure for the synthesis of acid-sensitive epoxides: Use of 1-methylimidazole as the additive on methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide

An effective method for suppression of ring opening and rearrangement of acid-sensitive epoxides during methyltrioxorhenium(MTO)-catalyzed epoxidation of alkenes with H2O2 by using 1-methylimidazole as a co-additive has been found. The combined use of 3-methylpyrazole and 1-methylimidazole as the additives has been found to be an effective procedure that affords excellent yields of acid-sensitive epoxides for MTO-catalyzed epoxidation.

Oxidative cyclization of alkenols with Oxone using a miniflow reactor

A miniflow system for oxidative cyclization of alkenols with Oxone was developed. Thus, the oxidative cyclization of (Z)- and (E)- alkenols in i-PrOH with an aqueous solution of Oxone proceeded smoothly and safely in a PTFE tube without any exogenous catalytic species, and was subsequently quenched in a flow-reaction manner to afford the corresponding furanyl and pyranyl carbinols quantitatively within 5 or 10 min of residence time.

Tightly convoluted polymeric phosphotungstate catalyst: An oxidative cyclization of alkenols and alkenoic acids

Equation Presented A tightly convoluted polymeric phosphotungstate catalyst was prepared via ionic assembly of H3PW12O40 and poly(alkylpyridinium). An oxidative cyclization of various alkenols and alkenoic acids was efficiently promoted by the polymeric catalyst in aq H 2O2 in the absence of organic solvents to afford the corresponding cyclic ethers and lactones in high yield. The catalyst was reused four times without loss of catalytic activity.

One-pot regio- and stereoselective cyclization of 1,2,n-triols

A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright

Oxidative cyclization of 5-hydroxyalkenes with rhenium oxide, utilizing a co-oxidant. IV

5-Hydroxylalkenes react with rhenium(VII) oxide in the presence of another oxidant, H5IO6, to provide substituted tetrahydrofurans. The yield and stereoselectivity are comparable to stoichiometric results.

Directed oxidative cyclization of 5-hydroxyalkanes with rhenium oxide

5-Hydroxyalkenes react with rhenium(VII) oxide (Re2O7) to provide 2-hydroxymethyltetrahydrofurans. Oxidative cyclization occurs with overall syn addition to the alkenes in moderate yields with little tendency toward oxidation of alcohols to carbonyl compounds.