Abstract
The reaction of ethylene carbonate (1) with pentane-2,4-dione (2) was carried out in the presence of a series of halides as catalysts. As examples, the reaction catalysed by sodium iodide gave 4-oxopentyl acetate (3), and that catalysed by tetraethylammonium chloride gave 2-methyl-2-(2-oxopropyl)-1.3-dioxolan (4), as the predominant product in high yield. Reactions with 1,3-diphenylpropane-1,3-dione (11) in place of (2) showed the same trend. However, reactions with 2-alkyl-1,3-diphenylprop-ane-1,3-diones, (20) and (25), gave no oxoalkyl esters corresponding to (3), but other types of product [(21), (22), and (26)]. In reactions with 3,3-dibenzylpentane-2,4-dione (30), which has no proton dissociable under the conditions used, were obtained 3-benzyl-4-phenylbutan-2-one (31), 2-(2-acetoxyethoxy)-3-benzyl-4-phenylbut-2-ene (32), and 2-hydroxy-ethyl acetate (33). Reaction mechanisms are discussed.Moreover, ethyl acetoacetate (34) anddiethyl malonate (35) gave lactone derivatives, (37) and (39), respectively, but diethyl 2-acetamidomalonate (36) gave ethyl 2-acetamidobutyrate (40), in reactions with (1). Furthermore, the reactions of (1) with the diones (2) and (11) in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) gave the corresponding ethylene acetals (4) and (16), respectively.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
