3491-32-5Relevant academic research and scientific papers
CHLORINATED POLYETHER AND POLYURETHANE OBTAINED THEREFROM
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, (2011/06/19)
Provided is a chlorinated polyether which has excellent solubility in solvents and excellent thermal stability, has the excellent effect of improving the adhesion of coating materials, inks, and adhesives to polyolefins, can be expected to be usable as a flame retardant, and is useful also as a novel starting material for polyurethanes. The polyether is a novel chlorinated polyether containing, as a repeating unit, at least one of the chlorinated-ether residue represented by the following formula (1) and the chlorinated-ether residue represented by the following formula (2). Also provided is a novel polyurethane obtained therefrom.
Preparation and reactions of 2-chloro-3,4-epoxy-1-butene: a convenient route to (Z)-3-chloroallylic alcohols.
Taber, Douglass F,Mitten, Jeffrey V
, p. 3847 - 3851 (2007/10/03)
Epoxide 2 was prepared from 3,4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe(2)-mediated S(N)2' addition of sp(2)- or sp(3)-hybridized Grignard reagents to 2-chloro-3,4-epoxy-1-butene (2) afforded (Z)-3-chloroallylic alcohols such as 3 in good yields and with high regio- and stereoselectivity.
In vitro metabolism of chloroprene: Species differences, epoxide stereochemistry and a de-chlorination pathway
Cottrell,Golding,Munter,Watson
, p. 1552 - 1562 (2007/10/03)
Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.
Ionic and Radical Addition of Chlorine, Bromine and Some Halogen Systems of Butadiene Monoxide
Shellhamer, Dale F.,Green, Richard C.,Luttrull, Jeffrey K.,Seneker, Stephan D.,Potter, Mark K.,et al.
, p. 229 - 232 (2007/10/02)
Ionic reactions of bromine, chlorine, methyl hypochlorite or N-bromosuccinimide with butadiene monoxide (4) give only 1,2-addition products.The Markownikoff (1-halo-2-methoxy-3,4-epoxybutane) and anti-Markownikoff (2-halo-1-methoxy-3,4-epoxybutane) product ratios for ionic reaction of methyl hypochlorite and N-bromosuccinimide in methanol with 4 are similar to those obtained with 1-hexene.These data indicate that a rather symmetrical halonium ion is formed in the ionic halogenation of 4.Free radical reaction of bromine, chlorine, or trichloramine to 4 does not give ring-opened products as one might expect for formation of an epoxy carbonyl intermediate.The mechanistic implications from these observations are discussed.
