16108-63-7Relevant academic research and scientific papers
Syntheses of Dialkyl and Functionalized Ketones via 1-(Benzotriazol-1-yl)alkyl Methyl Thioethers
Katritzky, Alan R.,Oniciu, Daniela C.,Ghiviriga, Ion,Soti, Ferenc
, p. 2110 - 2115 (2007/10/03)
Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl)alkyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isocyanate: the products were readily hydrolyzed to α-functionalized ketones in dilute aqueous acid.
Synthesis of α-Hydroxy Ketones by Direct, Low-Temperature, in Situ Nucleophilic Acylation of Aldehydes and Ketones by Acyllithium Reagents
Seyferth, Dietmar,Weinstein, Robert M.,Hui, Richard C.,Wang, Wei-Liang,Archer, Colin M.
, p. 5620 - 5629 (2007/10/02)
The reaction of n-, sec-, and tert-butyllithium with CO at atmospheric pressure at -110 and -135 deg C in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC(O)Li, which reacts with the carbonyl compound to give the α-hydroxy ketone, generally in good yield.Reactions with aldehydes are limited in scope, working well with the t-BuLi-derived acyllithium reagents, but not with n-BuC(O)Li.
HIGH YIELD ACYL ANION TRANSFER REACTIONS: NUCLEOPHILIC ACYLATION OF ALDEHYDES
Seyferth, Dietmar,Weinstein, Robert M.,Wang, Wei-Liang,Hui, Richard C.
, p. 4907 - 4910 (2007/10/02)
Aldehydes be may acylated to give R'CH(OH)C(O)R in good yield by the RLi/CO in situ procedure at very low temperatures.Examples are given of ketone acylations which demonstrate the advantages of 1:1 RLi/substrate stoichiometry and the use of lower (-135 deg C) temperature.
High-Yield Acyl Anion Trapping Reactions: Syntheses of α-Hydroxy Ketones and 1,2-Diketones
Seyferth, Dietmar,Weinstein, Robert M.,Wang, Wei-Liang
, p. 1144 - 1146 (2007/10/02)
The in situ generation of n-C4H9C(O)Li by the reaction of n-C4H9Li with CO at -110 deg C in the presence of ketones gives good (50-90percent) yields of α-hydroxy ketones.When the n-C4H9C(O)Li reaction is carried out in the presence of esters, good (65-80percent) yields of α-diketones are obtained, thus demonstrating that RC(O)Li can be reagents of practical utility.Similar reactions were observed with sec-C4H9Li and tert-C4H9Li.
