99309-89-4Relevant academic research and scientific papers
Organophosphorous chemistry: Selective transformation of benzoin to benzil, desyl bromide, or benzyl phenyl ketone
Furukawa, Isao,Sasaki, Mitsuhiro,Inoue, Takeshi,Ohta, Tetsuo
, p. 85 - 99 (2007/10/03)
Reaction of benzoin with dibromotriphenylphosphorane under various conditions has been closely investigated. Benzoin was selectively converted to desyl bromide by treatment with dibromotriphenylphosphorane in the presence of triethylamine, while benzyl phenyl ketone was formed in the presence of an excess amount of triphenylphosphine. On the other hand, benzoin was effectively oxidized to benzil by treatment with only bromine. The mechanism of producing these was also proposed. Desyl bromide was formed from the reaction of benzoin with dibromotriphenylphosphorane as a primary product and converted to benzyl phenyl ketone via the Perkow reaction, and benzil was formed by the oxidation of benzoin by bromine. When triethylamine or triphenylphosphine was used as an added base, these bases trapped free bromine, and the oxidation product, benzil, was formed in low yield. In the presence of triphenylphosphine as a base, the Perkow reaction of desyl bromide proceeded smoothly to give benzyl phenyl ketone preferentially, while in the presence of triethylamine, replacement of the hydroxy group to bromide occurred mainly.
A VERSATILE REAGENT FOR SYNTHESIS OF α-HYDROXY ALDEHYDES AND KETONES --- METHYLTHIOMETHYL p-TOLYL SULFONE
Ogura, Katsuyuki,Tsuruda, Toshihiko,Takahashi, Kazumasa,Iida, Hirotada
, p. 3665 - 3668 (2007/10/02)
Methylthiomethyl p-tolyl sulfone (1) can be utilized for synthesizing α-hydroxy ketones as well as α-hydroxy aldehydes, the hydroxyl group of which is protected with acetyl, tetrahydropyranyl, or methoxymethyl group.
Tandem Alkylation-Reduction. Highly Stereoselective Synthesis of (E)-1-Hydroxymethyl Methyl Propenyl Ethers from Aldehydes Using 1-Lithio-1-methoxyallene
Weiberth, Franz J.,Hall, Stan S.
, p. 5308 - 5314 (2007/10/02)
Tandem alkylation-reduction of a series of aldehydes, by alkylating with 1-lithio-1-methoxyallene followed by reducing with lithium-ammonia, regiospecifically and highly stereoselectively affords the 1-hydroxymethyl methyl propenyl ether in which the alkene geometry is exclusively E.Aldehydes that have been subjected to this convenient procedure include aromatic, aliphatic, and heterocyclic aldehydes.Subsequent hydrolysis, in the aromatic and aliphatic cases, affords the corresponding α-hydroxy ethyl ketones.The stereochemistry of the propenyl ethers was established by 13C NMR spectroscopy.A mechanism for the selective reduction of the methoxyallene system is proposed.
