86335-72-0Relevant academic research and scientific papers
Stabilization of reactive aldehydes by complexation with methylaluminum bis(2,6-diphenylphenoxide) and their synthetic application
Maruoka, Keiji,Concepcion, Arnel B.,Murase, Noriaki,Oishi, Masataka,Hirayama, Naoki,Yamamoto, Hisashi
, p. 3943 - 3949 (2007/10/02)
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.
Reaction of Enol Ethers with Formaldehyde and Organoaluminum Compounds
Snider, Barry B.,Phillips, Gary B.
, p. 2789 - 2792 (2007/10/02)
Reaction of formaldehyde and trimethylaluminum with an enol ether derived from an aldehyde gives the adduct resulting from addition of hydroxymethyl and methyl groups to the enol ether double bond.The threo isomer is formed selectively (90-95percent) from
