1,3-Butadiene monoxide

Scientists at DuPont Merck Pharmaceuticals [31] had also developed a new process to prepare 37, based on a modification of the Corey-Fuchs method, from cyclopropylaldehyde, prepared by thermal rearrangement of butadiene monoxide. [Pg.24]

Sharief Y, Brown AM, Backer LC, et al. 1986. Sister chromatid exchange and chromosome aberration analyses in mice after iruvivo exposure to acrylonitrile, styrene, or butadiene monoxide. Environ Mutagen 8 439-448. [Pg.118]

A wide variety of new approaches to the problem of product separation in homogeneous catalysis has been discussed in the preceding chapters. Few of the new approaches has so far been commercialised, with the exceptions of a the use of aqueous biphasic systems for propene hydroformylation (Chapter 5) and the use of a phosphonium based ionic liquid for the Lewis acid catalysed isomerisation of butadiene monoxide to dihydrofuran (see Equation 9.1). This process has been operated by Eastman for the last 8 years without any loss or replenishment of ionic liquid [1], It has the advantage that the product is sufficiently volatile to be distilled from the reactor at the reaction temperature so the process can be run continuously with built in product catalyst separation. Production of lower volatility products by such a process would be more problematic. A side reaction leads to the conversion of butadiene oxide to high molecular weight oligomers. The ionic liquid has been designed to facilitate their separation from the catalyst (see Section 9.7)... [Pg.237]

Grignard compounds in the thiophene series were studied (20) and used for the synthesis of some thienylbutenols. The product obtained by the reaction of alpha-thienylmagnesium bromide with butadiene monoxide has been identified as 4-(2-thienyl)-buten-2-ol-l formed by 1-4 addition. Furthermore, the Grignard compounds were utilized for... [Pg.139]

Fig. 10.25. Reaction pathway of butadiene monoxide (10.102) in aqueous NaCl solution to yield l,2-dichloro-3,4-epoxybutane (10.111) [168], The sequence involves the intermediate...

Solvolysis of butadiene monoxide (10.102) in saline solution is a rather unexpected reaction that further documents this compound s reactivity [168]. In aqueous NaCl solution at physiological pH and temperature, butadiene monoxide disappeared rapidly to form 1,2-dichloro-3,4-epoxybutane (10.111, Fig. 10.25). There was a linear dependence of the rate of reaction on the Cl concentration (in the range investigated (34-135 mM)). The reaction pathway was described as slow solvolytic formation of the bu-tenylchloronium ion, followed by Cl attack to yield Cl2 and butadiene. Cl2 is then rapidly trapped by a second molecule of butadiene monoxide to form a different chloronium ion that also reacts with Cl to yield the final, stable dichloro product (10.111). The formation of 1,2-dichloro-3,4-epoxy-butane under physiological conditions is believed to be toxicologically significant. [Pg.654]

A. A. Elfarra, R. J. Krause, R. R. Selzer, Biochemistry of 1,3-Butadiene Metabolism and Its Relevance to 1,3-Butadiene-Induced Carcinogenicity , Toxicology 1996, 113, 23 - 30 R. A. Kemper, R. J. Krause, A. A. Elfarra, Metabolism of Butadiene Monoxide by Freshly Isolated Hepatocytes from Mice and Rats Different Partitioning between Oxidative, Hydrolytic, and Conjugations Pathways , Drug Metab. Dispos. 2001, 29, 830 - 836. [Pg.676]

X. Cheng, C. Manigher-Poulet, D. Ross, J. A. Ruth, Solvolytic Formation of 1,2-Di-chloro-3,4-epoxybutane from Butadiene Monoxide under Physiological Conditions , Drug Metab. Dispos. 1994, 22, 206 - 210. [Pg.676]

In the reactions of styrene oxide and butadiene monoxide with ester carbanions, attack takes place at both primary and secondary epoxy carbon atoms.The findings provide evidence for the participation of the conjugative effect in the ring opening of these epoxides. [Pg.327]

Bechtold, W.E., Strunk, M.R., Thomton-Maiming, J.R. Henderson. R.F. (1995) Analysis of butadiene, butadiene monoxide, and butadiene diepoxide in blood by gas chromatography/ gas chromatography/mass spectroscopy. Chem. Res. Toxicol., 8, 182—187... [Pg.204]

Elfarra, A.A., Duescher, R.J. Pasch, C.M. (1991) Mechanism of 1.3-butadiene oxidations to butadiene monoxide and crotonaldehyde by mouse liver microsomes and chloroperoxidase. Arch. Biochem. Biophys., 286, 244-251... [Pg.207]

Elfarra, A.A., Sharer, J.E. Duescher, R.J. (1995) Synthesis and characterization of Wacetyl-L-cysteine S-conjugates of butadiene monoxide and their detection and quantitation in urine of rats and mice given butadiene monoxide. Chem. Res. Toxicol.. 8, 68-76... [Pg.207]

Filser, J.C. Bolt, H.M. (1984) Inhalation pharmacokinetics based on gas uptake studies VI. Comparative evaluation of ethylene oxide and butadiene monoxide as exhaled reactive metabolites of ethylene and 1,3-butadiene in rats. Arch. Toxicol., 55, 219-223... [Pg.208]

Johanson. G. Filser, J.G. (1993) A physiologically based pharmacokinetic model for butadiene and its metabolite butadiene monoxide in rat and mouse and its significance for risk extrapolation. Arch. Toxicol., 61, 151-163... [Pg.211]

Krause. R.J. Elfarra, A.A. (1997) Oxidation of butadiene monoxide to meso- and (+-)-diepoxy-butane by cDNA-expressed human cytochrome P450s and by mouse, rat, and human liver microsomes evidence for preferential hydration of /MC5o-diepoxybutane in rat and human liver microsomes. Arch. Biochem. Biophys., 337, 176-184... [Pg.212]

Maniglier-Poulet. C.. Cheng, X., Ruth, J.A. Ross, D. (1995) Metabolism of 1,3-butadiene to butadiene monoxide in mouse and human bone marrow cells. Chem.-biol. Interact., 91, 119-129... [Pg.214]

Neagu, 1., Koivisto, R, Neagu, C., Kostiainen, R., Stenby, K. Peltoncn, K. (1995) Butadiene monoxide and deoxyguanosine alkylation products at the N7-position. Caremogenesis. 16, 1809-1813... [Pg.216]

Selzer, R.R. Elfarra, A. A. (1996a) Synthesis and biochemical characterization of AT-, AT-, and AT-guanosine adducts of butadiene monoxide. Chem. Res. Toxicol., 9, 126-132... [Pg.219]

Selzer, R.R. Elfarra, A.A. (1997a) Characterization of four V-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide. Carcinogenesis, 18, 1993-1998... [Pg.219]

Sharer, J.E. Elfarra, A.A. (1992) A -(2-Hydroxy-3-buten-l-yl)glutathione and A -(l-hydroxy-3-buten-2-yl)glutathione are in vivo metabolites of butadiene monoxide detection and quantitation in bile. Chem. Res. Toxicol., 5, 787-790... [Pg.219]

Sharer, J.E., Duescher, R.J. Elfarra, A.A. (1992) Species and tissue differences in the microsomal oxidation of 1,3-butadiene and glutathione conjugation of butadiene monoxide in mice and rats. Drug Metah. Disp., 20, 658-664... [Pg.220]

Tsuruta,T., Inoue,S., Tsubaki,K. Polymerization of styrene oxide and butadiene monoxide by organozinc compounds. Makromol. Chem. Ill, 236 (1968). [Pg.109]

Butadiene monoxide, 31, 3 Butane, 1,4-dhodo-, 30, 33 1,4-dinitro-, 34, 37 2-Butanone, 3-acetamido-, 33,1 terl-Butyl acetate, 34, 28 tt-BuTYLACETYI.ENE, 30, IS... [Pg.54]

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See also in sourсe #XX -- [ Pg.3 , Pg.31 ]

See also in sourсe #XX -- [ Pg.3 , Pg.31 ]

See also in sourсe #XX -- [ Pg.3 , Pg.31 ]

See also in sourсe #XX -- [ Pg.3 , Pg.31 ]

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