2,2,6-Trimethyl-4H-1,3-dioxin-4-one (TMD): A versatile acetylketene equivalent
Australian Journal of Chemistry, ISSN: 0004-9425, Vol: 65, Issue: 3, Page: 299-300
2012
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Conference Paper Description
A study was conducted to demonstrate 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD) as a versatile equivalent of acetylketene. A vinylogous aldol reaction was reported in which TMD was deprotonated by lithium diisopropylamide (LDA). The vinylogous enolate added nucleophilically to the carbonyl derivative, resulting in the formation of TMD derivatives. 5-halo-2,2,6-trimethyl-4H-1,3-dioxin-4-one was prepared by an electrophilic substitution reaction on the vinylic carbon a to the carbonyl group of TMD by using N-iodo- orN-bromosuccinimide. The bromo-and iodo- TMD derivatives were used as substrates in Suzuki-Miyaura reactions. The preparation of acetoacetamides by reaction of TMD with alkoxy alkylamines in refluxing xylene was demonstrated. Diazo transfer with methanesulfonyl azide afforded 2-diazoacetamides, which provided 2-diazo-acetanilides in high yields upon elimination of the acetyl group with LiOH.
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