58105-49-0Relevant academic research and scientific papers
Allylation of Alcohols and Carboxylic Acids with Allyl Acetate Catalyzed by [Ir(cod)2]+BF4- Complex
Nakagawa, Hideto,Hirabayashi, Tomotaka,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 3474 - 3477 (2007/10/03)
A facile method for the synthesis of allyl alkyl ethers from alcohols with allyl acetate was developed by the use of [Ir(cod)2] +BF4- complex. For instance, the reaction of allyl acetate with n-octyl alcohol in the presence of a catalytic amount of [Ir(cod)2]+BF4- complex afforded allyl octyl ether in quantitative yield. Allyl carboxylates were also prepared by the exchange reaction between carboxylic acids and allyl acetate in good yields. The [Ir(cod)2]+BF4- complex catalyzed the reaction of alkyl and aromatic amines with allyl acetate to lead to the corresponding allylamines in fair to good yields.
Solvent effects in deamination reactions
Banert, Klaus,Bunse, Michael,Engbert, Theodor,Gassen, Karl-Rudolf,Kurnianto, Apriana W.,Kirmse, Wolfgang
, p. 272 - 278 (2007/10/02)
Nitrous acid deaminations of (S)-2-butanamine, (2R,3S)-3-methyl-2-pentanamine (8), cyclopropananmine (17) and 4,4-dimethyl-2-adamantanamine (30) have been studied in water and in a series of carboxylic acids of decreasing polarity (acetic, 3,3-dimethylbutyric, 2-ethylhexanoic acid).The stereochemistry of aqueous deaminations varies from predominant inversion to predominant retention, depending upon the structure of the substrate (steric hindrance, neighbouring-group participation, etc.).In carboxylic acid media, alcohols arise with predominant retention, i.e. by front-side attack of the "internal" nucleophile (water).Inverting displacement of nitrogen by the "external" nucleophile (carboxylic acid/carboxylate) increases with decreasing polarity of the solvent.Even cyclopropanamine yields cyclopropyl esters (2-10percent) of inverted configuration, as shown with the aid of deuterium labels.Current mechanistic concepts are modified to account for these results.
