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• 15409-53-7 6-methyl-2-(hydroxymethylene)cyclohexanone 
• 110-88-3 1,3,5-Trioxan 
• 13670-83-2 6-methylcyclohexanone lithium enolate 
• 50-00-0 formaldehyd 
• 19980-33-7 6-methyl-1-trimethylsiloxycyclohex-1-ene 
• 583-60-8 2-Methylcyclohexanone 

Relevant academic research and scientific papers

Aldol Synthesis with an Aqueous Solution of Formalin

With an aqueous solution of formalin, aldol reaction of trimethylsilyl enol ether proceeds moderately using tetrabutylammonium fluoride (TBAF). Furthermore, catalytic asymmetric hydroxymethylation with trimethoxysilyl enol ether using water tolerant (R)-B

Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis

Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.

Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media

Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)3), were found to be stable Lewis acids in water.In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde

Stabilization of reactive aldehydes by complexation with methylaluminum bis(2,6-diphenylphenoxide) and their synthetic application

Reactive aldehydes such as formaldehyde and α-chloro aldehydes can be successfully generated by treatment of readily available trioxane and α-chloro aldehyde trimers, respectively, with methylaluminum bis(2,6-diphenylphenoxide) (MAPH), and stabilized as their 1:1 coordination complexes with MAPH. The resulting CH2=O·MAPH complex reacts with a variety of olefins to furnish ene-reaction products with excellent regio- and stereoselectivities. In addition, this complex as well as α-chloro aldehyde-M APH complexes can be utilized as a stable source of gaseous formaldehyde and reactive α-chloro aldehydes, respectively, for the nucleophilic addition of various carbanions (organometallics, enolates, etc.). Formation of reactive aldehyde-MAPH complexes is firmly confirmed by 1H NMR spectroscopy. A space-filling model of aldehyde-M APH complexes implies that formaldehyde and α-chloro aldehydes coordinated with MAPH may be electronically stabilized by two parallel phenyl groups of aluminum ligands.

Lanthanide Trifluoromethanesulfonates as Stable Lewis Acids in Aqueous Media. Yb(OTf)3 Catalyzed Hydroxymethylation Reaction of Silyl Enol Ethers with Commercial Formaldehyde Solution

Silyl enol ethers smoothly react with commercial formaldehyde solution to give the corresponding hydroxymethylated adducts in high yields by the promotion of a catalytic amount of ytterbium(III) triflate (Yb(OTf)3), which is a stable Lewis acid in aqueous