3173-79-3

Usage

Type of compound

Lactone (cyclic ester)

Contains

Beta-propiolactone structure

Usage

Monomer in production of polymers and resins, crosslinking agent in synthesis of silicone materials

Reactivity

High

Polymerization reactions

Capable of undergoing

Importance

Versatile building block in the chemical industry

Safety precautions

Potential irritant to skin, eyes, and respiratory system; possible environmental toxicity risk

InChI:InChI=1/C8H12O2/c1-5(2)6-8(3,4)7(9)10-6/h1-4H3

Upstream product

• 598-26-5 dimethylketene 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 933-52-8 2,2,4,4-tetramethyl-1,3-cyclobutanedione 

Downstream Products

• 32674-66-1 3-(Dipropoxy-phosphanyloxy)-2,2,4-trimethyl-pent-3-enoic acid propyl ester 
• 32674-88-7 2,2,4-Trimethyl-3-(methyl-phenoxy-phosphinoyloxy)-pent-3-enoic acid methyl ester 
• 32674-87-6 3-(Methoxy-methyl-phosphinoyloxy)-2,2,4-trimethyl-pent-3-enoic acid phenyl ester 
• 32687-25-5 Dimethyl-phosphoramidous acid 1-(1-dimethylcarbamoyl-1-methyl-ethyl)-2-methyl-propenyl ester phenyl ester 
• 10472-30-7 2,2,4,4-Tetramethyl-3,5-dioxo-5-phenyl-pentanoic acid 
• 10472-34-1 2,2,4-Trimethyl-3-oxo-valerylchlorid 
• 778-18-7 hexamethylcyclohexane-1,3,5-trione 
• 10472-29-4 5-hydroxy-5-isopropyl-2,2,4,4,6,6-hexamethyl-cyclohexane-1,3-dione 
• 10472-36-3 2,2,4,4,6,6,8,8-Octamethyl-3,5,7-trioxo-nonanedioic acid 
• 33471-75-9 2.2.4-Trimethyl-3-oxovaleriansaeure-N-m-methoxyphenylamid 
• 24388-84-9 N-cyclohexyl-2,2,4-trimethyl-3-oxo-pentanamide 
• 43050-51-7 2.2.4-Trimethyl-3-oxovaleriansaeure-N-p-methoxyphenylamid 
• 24388-85-0 2,2,4-Trimethyl-3-oxovaleriansaeure-N-n-butylamid 
• 7206-04-4 2.2.4-Trimethyl-3-oxovaleriansaeure-N-phenylamid 

Relevant academic research and scientific papers

Phosphine-catalyzed stereoselective dimerizations of ketenes

Full details of optimisation studies of the phosphine-catalyzed ketene homodimerization reaction and the detailed development of an asymmetric variant are discussed. Studies towards the development of a phosphine-catalyzed ketene heterodimerization reaction are revealed. A discussion of possible reaction mechanisms for the dimerization reactions, supported by spectroscopic analysis of intermediates and trapping experiments, is also presented.

Josiphos-catalyzed asymmetric homodimerization of ketoketenes

In this paper the development of a chiral phosphine-catalyzed homodimerization of ketoketenes that provides access to a variety of highly substituted ketoketene dimer β-lactones (11 examples) is reported. The Josiphos catalytic system displays good to exc

Mechanistic studies of the phosphine-catalyzed homodimerization of ketoketenes

The mechanism of PBu3-catalyzed homodimerization of ketoketenes has been explored and compared with that of the previously reported trialkylphosphite-mediated reactions. NMR studies of the PBu3- catalyzed reaction implicated the involvement of tetravalent phosphonium intermediates. Phosphonium intermediates in the catalytic cycle were trapped through reaction with trimethylsilyl chloride and 4-chlorobenzaldehyde, and the resulting products were characterized. A method for the stoichiometric generation of phosphonium enolates was developed as a result of these studies. No evidence was obtained for the involvement of pentacovalent phosphorane intermediates in trialkylphosphine-catalyzed ketoketene homodimerization reactions, in contrast with the mechanism of the trialkylphosphite-mediated homodimerization of dimethylketene. An X-ray crystal structure analysis of methylphenylketene dimer showed that it possesses Z-geometry about the exocyclic olefin.

Insights into the formation of symmetrical trimers of dialkylated ketenes starting from acid chloride precursors

Application of known dialkyl ketene di- and trimerization to more complex precursors could readily open the route to highly functionalized symmetrical cyclobuta-1,3-diones and cyclohexa-1,3,5-triones. We report herein the results on three substrates containing either a C=C double bond or a protected glycol moiety as illustrative functionalized groups. The nature of the substituents is found to be crucial: while cyclopentenyl and more constrained dioxolanocyclopentenyl precursors efficiently dimerize, a diallylic derivative fails. At the millimolar scale, methoxide-catalyzed trimerization shows limited reproducibility, even for the reported substrate tetramethylcyclobuta-1,3-dione. However, systematic studies, including the use of microwaves, demonstrate that formation of symmetrical trimers is favored under solvent-free conditions and conventional heating, which allowed us to isolate and characterize trispiro[4.1.4.1.4.1]octadeca-2,9,15-triene-6,12,18-trione.

Ketene. Part 26. The Reactions of 3,4-Dihydroisoquinoline N-Oxide with Ketenes, and an Attempted Synthesis of 3,4-Dihydro-3,3-dimethylquinoline N-Oxide

3,4-Dihydroisoquinoline N-Oxide reacts with dimethylketene to form a 1:2 adduct (8) in addition to compounds (6) and (7).With cyano-t-butylketene and ethoxycarbonyl-t-butylketene the adducts (9a) and (9b) are formed. 3,3-Dimethyl-1,2,3,4-tetrahydroquinoline (21a) has been synthesized, but attempts to convert this into the nitrone (20b) were unsuccessful.