73805-25-1Relevant academic research and scientific papers
Synthesis of 4-[4′-bis(2″-chloroethyl)aminophenyl]-3,3,4,4-tetrafluorobutanoic acid [3,3,4,4-tetrafluorochlorambucil]
Buss, Christopher W.,Coe, Paul L.,Tatlow, John Colin
, p. 111 - 116 (2007/10/03)
Reaction of 2,2-dichloro-2-(4′-nitrophenyl)acetonitrile with mercury(II) oxide/pyridiniumpoly(hydrogen fluoride), (aqueous work-up), gave 2,2-difluoro-2-(4′-nitrophenyl)acetamide, from which were made the parent acid and thence its acid chloride. This and
Molecular Rearrangements. 13. Kinetics and Mechanism of Rearrangements of Some Ring-Substituted α-Chlorostyrene Oxides and trans-β-Chlorostyrene Oxides.
McDonald, Richard N.,Cousins, Raymond C.
, p. 2976 - 2984 (2007/10/02)
The synthesis of certain phenyl-substituted derivatives of the isomeric trans-β-chlorostyrene oxides (6) and α-chlorostyrene oxides (7) are reported.The kinetics of rearrangement of 6 (X = p-CH3, H, p-Br, m-Cl, p-NO2) to phenylchloroacetaldehydes (12) in CCl4 buffered by Na2HPO4 and 7 (X = p-CH3, H, p-NO2) to ω-chloroacetophenones in CCl4 were determined by following the rates of disappearance of the α-chloro epoxide and formation of the α-chloro carbonyl product.These substituent effects at 130 deg C were correlated with ?+ constants, yielding ρ values of-3.5 and -0.57 for the rearrangements of 6 and 7, respectively.In nitrobenzene solvent, the kC6H5NO2/kCCl4 for 6 was 180 and for 7 was 1740, the latter solvent effect attributed to nucleophilic solvent participation.It was concluded that these thermal rearrangements of 6 and 7 occur by disrotatory Cβ-O bond heterolysis to yield the corresponding α-keto carbonium-chloride ion pairs.
