3 -chloro -4- -furanone

Treatment of the 1,5-diene (Z,Z)-CHD=CHCH2CH2CH=CHD with potassium permanganate results in stereospecific oxidative cycloaddition to give 40% of the tetrahydrofuran (25), which possesses four chiral centres the (E,E)-isomer behaves in an analogous fashion. " 2,2-Dialkoxytetrahydrofurans are formed from epoxides and keten acetals thus epichlorhydrin reacts with MeCH=C(OMe)2 in the presence of zinc chloride to afford compound (26). The chloro-furanone (27) is obtained as a mixture of cis- and trans-isomers from styrene and trimethylsilyl dichloroacetate in the presence of bis(triphenylphos-phine)ruthenium(ii) chloride. Total syntheses of both enantiomers of the pheromone (28) of the Japanese beetle [Popillia japonica) and of chalcogran (29), the principal pheromone of Pityogenes chalcographus (L.), have been described. 

Kronberg L, Vartiainen T (1988) Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and of its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. Mutat Res 206 177-182... 

Suzuki N, Nakanishi J (1995) Brominated analogues of MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2 (5H)-furanone) in chlorinated drinking water. Chemosphere 30 1557-1564... 

Komulainen H, Kosma VM, Vaittinen SL, Vartiainen T, Kaliste-Korhonen E, Lotjonen S, Tuominen RK, Tuomisto J (1997) Carcinogenicity of the drinking water mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone in the rat. J Nat Cancer Inst 89 848-856... 

Disinfection by-products (DBPs) form an undesired species in the chlorine disinfection processes of waters (performed with chlorine, chlorine dioxide, and chloramines). The high priority DBPs include brominated, chlorinated, and iodinated species of halomethanes, brominated, and chlorinated forms of haloacetonitriles, haloketones, haloacids, and halonitromethanes, as well as analogues of 3-chloro-(4-dichloromethyl)-5-hydroxy-2(5//)-furanone. All the high priority DBPs included in the Nation-wide DBP occurrence study are listed in Table 18.1 together with other contaminants. 

B. 7-Chloro-7-cyanobicyclo[4.2.0]octan-8-one. To a 250-mL Erlenmeyer flask is added 20.0 g (94.8 mmol) of 3,4-dichloro-5-isopropoxy-2(5H)-furanone and 120 mL of methanol. The flask is cooled in an ice bath with stirring and 7.5 g (115.4 mmol) of sodium azide is added. The ice bath is removed after 15 min and the mixture is stirred for an additional 50 min. After dilution with 600 mL of water, the reaction mixture is extracted with one 100-mL and two 50-mL portions of toluene. The combined organic layers are washed with water (2 x 100 mL) and with 100 mL of brine and are dried with magnesium sulfate. TLC analysis (1 1 ethenhexane, S1O2) indicates only one component (Rf = 0.38) and no remaining dichlorofuranone (Rf = 0.45) (Note 3). 

B. Holmbom, L. Kronberg, P. Bachlund, V. Langvic, J. Hemming, M. Reunanen, A. Smeds and L. Tikannen. Formation and properties of of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5J7)-furanone, a potent mutagen in chlorinated waters , in Water Chlorination Chemistry, Environmental Impact, and Health Effects (Eds. R. L. Jolley, L. W. Condie, J. D. Johnson,... 

Cyclopropyl isocyanates react effectively with various nucleophilic reagents. Ammonia and amines yield urea derivatives, " alcohols and phenols afford carbama-tg5,i5 5,164,181,184,185 )V )y-dimethylhydrazine gives a semicarbazide derivative, whereas cyclo-propylammonium chlorides are obtained in refluxing hydrochloric acid. The yields are usually very good. When more highly functionalized nucleophiles are employed, such as the enolate from ethyl 4-chloro-3-oxobutanoate, more complex molecules can be obtained, e.g. the formation of furanone derivative 15. ... 

Maki-Raakkanen, J., and Hakulinen, R. (2008). Assesssment of the genotoxicity of the rat carcinogen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5//)-furanone (MX) in rat liver epithelial cells in vitro. Toxicol in Vitro 22, 535-640. 

Ethyl 2-amino-l,4,5,6-tetrahydropyridine-3-carboxylate (13) is obtained under mild conditions by mutual treatment of 3-carbethoxy-2-piperidinone (12) with triethyloxonium tetrafluoroborate and then ammonia.13 The synthesis of /J-enamino esters such as 2-amino-l-aryl-3-carbethoxypyrrolin-4-one (15) possessing a carbonyl function in the partially saturated ring is accomplished by cyclization of ethyl y-chloro-oc-cyano-acetoacetate (14) with arylamines.14 As H-NMR spectra show, 15 exists predominantly in the / -dicarbonylenamine form (Scheme 5). Furthermore, furanones of the general... 

When the nitrate ester 277 was treated with BuaSnD and AIBN, the deuteriated alcohol 278 was formed, by 1,5-radical translocation. However, the 2 -chloro-2 -deoxy-system 279 gave the furanone 280 under the same conditions. These results suggest that the inhibition of ribonucleoside diphosphate reductase by 2 -chloro-2 -deoxynucleosides involves loss of Cl from a radical at C-3. Some related studies from the same team, also supporting this conclusion, were mentioned earlier. ... 

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