6050-53-9Relevant academic research and scientific papers
Imidoyl chlorides as starting materials for the preparation of masked acyllithium intermediates: Synthetic applications
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 12007 - 12028 (2007/10/03)
The lithiation of several imidoyl chlorides 5, catalysed by substoichiometric amounts of naphthalene, followed by reaction with different electrophiles gives, after hydrolysis, the corresponding imine derivatives 6 and 9 or amines 7, depending on the reac
Imidoyllithiums: Masked acyllithium reagents
Alonso, Emma,Ramon, Diego J.,Miguel, Yus
, p. 8903 - 8906 (2007/10/03)
The reaction of chloroimines 1 with an excess of lithium powder and a catalytic amount of naphthalene (4 mol %) in THF at -78°C leads to the corresponding imidoyllithium intermediates 2, which by treatment with different electrophiles [PriCHO, Bu(t)CHO, n-C5H11CHO, PhCHO, Et2CO, (CH2)5CO, EtOCOCl, MeOCSCl, n-C7H15CON(Me)OMe] at -78 to 20°C and final hydrolysis with water affords functionalysed imines 3. For starting material la is necessary to filter off the excess of lithium at the end of the lithiation step in order to get compounds 3, without filtration amines 4 are the reaction products isolated. Hydrolysis of compounds 3 either during chromatographic purification or by acidic hydrolysis (2 N HCl, THF) gives the expected functionalised ketones 5.
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.
Synthesis of α-Ketols Mediated by Divalent Samarium Compounds
Collin, Jacqueline,Namy, Jean-Louis,Dallemer, Frederic,Kagan, Henri B.
, p. 3118 - 3122 (2007/10/02)
Coupling reactions of acid chlorides are mediated by SmI2 and SmCp2, leading to α-ketols 3.Condensation reactions of acid chlorides on aldehydes similarly product α-ketols 5; with ketones, best results are obtained with use of SmI2.Reactivities of SmI2 and SmCp2 are compared and mechanisms of the reactions discussed.Formation of an acylsamarium species is shown.
