Acetone chloroacetone

Much research has been done on the synthesis of perhalogenated P-sultones. The sulfonation of acyclic fluorovinyl ethers leads to a product that is stable up to slightly above room temperature. Thermolysis decomposes the ring structure under SO2 evolution and formation of acid fluorides and perfluorocyclopropane (Eq. 78). )S-Sultones have been synthesized by addition of sulfonyl chlorides to perhalogenated ketones in the presence of triethylamine. The formation of the l-oxa-2-thiacyclobutane 2,2-dioxides appears to require an activated but sterically unhindered carbonyl group because acetone, chloroacetone, trifluoroacetophenone, and p-nitroaceto-phenone did not yield the desired products. ... 

Ketones Acetone, chloroacetone, methylethylketone and acetophenone FeCl4, InQ4 a... 

Given the number of reports describing aldol reactions with hydroxyacetone (39) as a donor, little work has been done with other a-heterosubstituted acetones. Chloroacetone seems to be a problematic nucleophile While the regio- and stereoselectivity of its reactions are satisfactory, the yields of a ti-aldols are low or moderate, regardless of the aldehyde used [68] a-Fluoroaldols such as anti-46 can be effectively synthesized using prolinol as a catalyst [69]. 

Redistilled commercial chloroacetone, b.p. 118-120°, is used. The compound is lachrymatory. It is prepared inter alia by the chlorination of acetone in the cold. 

Various 4-, 5-, or 4,5-disubstituted 2-aryIamino thiazoles (124), R, = QH4R with R = 0-, m-, or p-Me, HO C, Cl, Br, H N, NHAc, NR2, OH, OR, or OjN, were obtained by condensing the corresponding N-arylthiourea with chloroacetone (81, 86, 423), dichloroacetone (510, 618), phenacyichloride or its p-substituted methyl, f-butyl, n-dodecyl or undecyl (653), or 2-chlorocyclohexanone (653) (Method A) or with 2-butanone (423), acetophenone or its p-substituted derivatives (399, 439), ethyl acetate (400), ethyl acetyl propionate (621), a- or 3-unsaturated ketones (691), benzylidene acetone, furfurylidene acetone, and mesityl oxide in the presence of Btj or Ij as condensing agent (Method B) (Table 11-17). 

Some observations are important for improvement of the yield and for the elucidation of the mechanism of the Meerwein reaction. Catalysts are necessary for the process. Cupric chloride is used in almost all cases. The best arylation yields are obtained with low CuCl2 concentrations (Dickerman et al., 1969). One effect of CuCl2 was detected by Meerwein et al. (1939) in their work in water-acetone systems. They found that in solutions of arenediazonium chloride and sodium acetate in aqueous acetone, but in the absence of an alkene, the amount of chloroacetone formed was only one-third of that obtained in the presence of CuCl2. They concluded that chloroacetone is formed according to Scheme 10-50. The formation of chloroacetone with CuCl2 in the absence of a diazonium salt (Scheme 10-51) was investigated by Kochi (1955 a, 1955 b). Some Cu11 ion is reduced by acetone to Cu1 ion, which provides the electron for the transfer to the diazonium ion (see below). 

The chain process of the Meerwein reaction can be visualized as shown in Scheme 10-57. There are at least two likely termination reactions for the chain process, namely the addition of a chlorine atom from CuCl2 to the aryl radical (Scheme 10-58) or reaction of the aryl radical with a hydrogen atom of acetone, followed by the formation of chloroacetone (Scheme 10-59). 

Crystalline samples of syndiotactic poly(methyl methacrylate) (st-PMMA) may be obtained from chloroacetone 178). This guest could be completely replaced by a variety of other guest molecules such as acetone, 1,3-dichloroacetone, bromoacetone, pinacolone, cyclohexanone, acetophenone and benzene. The X-ray diffraction patterns for these inclusion compounds were similar. These data indicate that the st-PMMA chains adopt a helical conformation of radius about 8 A and pitch 8.85 A. The guest molecules are located both inside the helical canals and in interhelix interstitial sites. 

Ethyl isocyanide, 46, 76, 77 Ethyl a-(isopropylideneaminooxy)pro-pionate, from acetone oxime and ethyl a-bromopropionate, 48,120 hydrolysis of, 48,121 Ethylmagnesium bromide, use with ferric chloride in cyclization of di-chloroacetone /J-Lolylmagncsium bromide adduct to l-f>-tolyicy-clopropanol, 47,108 Ethyl a-methyl-/3-phenylcinnamate, 48, 79... 

The photolysis of chloroacetone with light of wavelength 3130 A. has been studied in detail by Strachan and Blacet.44 At room temperature, the negligible amounts of carbon monoxide, methyl chloride, methane, and ethane formed and the preponderance of hydrogen chloride and acetone in the products of photolysis, suggested that the primary step was of type C. 

SYNS ACETONYL CHLORIDE A-STOFF CHLORACETONE CHLOROACETONE CHLORO-ACETONE, stabilized pOT) CHLOROPROPANONE 1-CHLORO-2-PROPANONE MONOCHLORACETONE MONOCHLOROACETONE MONOCHLORO-ACETONE, inhibited pOT) MONOCHLOROACETONE, stabilized pOT) MONOCHLOROACETONE, unstabilized pOT) TONITE... 

Fr desgn for CWA of WWI bror acetone 80 chloroacetone 2C Military Air Transport... 

Chloroacetone was obtained by Riche in 1859 in electrolysing a mixture of hydrochloric acid and acetone. It was used in the last war, especially by the French, to replace bromoacetone during the period of bromine shortage (1914-15). 

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