624733-44-4

Upstream product

• 2550-36-9 Cyclohexylmethyl bromide 
• 188531-95-5 N-cyclobutylidene-(N',N'-dimethylamino)amine 
• 201230-82-2 carbon monoxide 
• 1520990-53-7 (E)-2-(cyclohexylmethylene)cyclobutan-1-one 

Downstream Products

• 624733-51-3 2-cyclohexylmethyl-1,1-dimethoxycyclobutane 
• 624733-57-9 1,1-dibromo-2-cyclohexylmethylcyclobutane 

Relevant academic research and scientific papers

Unexpected Pd/C-catalyzed room temperature and atmospheric pressure hydrogenation of 2-methylenecyclobutanones

Pd/C-catalyzed hydrogenation reaction of 2-methylenecyclobutanones (2-MCBones)occurs at their exocyclic C[dbnd]C sites regio-specifically to produce 2-substituted cyclobutanones, which are useful building blocks for the synthesis of drug and pesticide int

α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation

Hydroformylation utilizes dihydrogen, carbon monoxide, and a catalyst to transform alkenes into aldehydes. This work applies chiral bisdiazaphospholane (BDP)- and bisphospholanoethane-ligated rhodium complexes to the hydroformylation of a variety of alkenes to produce chiral tetrasubstituted aldehydes. 1,1′-Disubstituted acrylates bearing electron-withdrawing substituents undergo hydroformylation under mild conditions (1 mol % of catalyst/BDP ligand, 150 psig gas, 60 °C) with high conversions and yields of tetrasubstituted aldehydes (e.g., 13:1 regioselectivity, 85% ee, and 99% regioselectivity and >19:1 diastereoselectivity to tetrasubstituted aldehydes at rates >50 catalyst turnovers/hour. NMR studies of the noncatalytic reaction of HRh(BDP)(CO)2 with methyl 1-fluoroacrylate enable interception of tertiary alkylrhodium intermediates, demonstrating migratory insertion to acyl species is slower than formation of secondary and primary alkylrhodium intermediates. Overall, these investigations reveal how the interplay of sterics, electronics, and ring strain are harnessed to provide access to valuable α-tetrasubstituted aldehyde synthetic building blocks by promoting branched-selective hydroformylation.

A Novel Route to Geminal Dibromocyclobutanes: Syntheses of 2-Substituted Cyclobutanone Acetals and Their Reaction with Boron Tribromide

Nine 2-substituted cyclobutanone acetals, in addition to the parent cyclobutanone acetal, were synthesized from their corresponding cyclobutanones and subsequently treated with boron tribromide. The substituents were either alkyl chains or a phenyl and a