Reduction of nitro- and nitroso-compounds by tervalent phosphorus reagents. Part III. Kinetic study of the triethyl phosphite reduction of 2-nitrosobiphenyl to carbazole
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 883-885
- https://doi.org/10.1039/j29690000883
Abstract
The triethyl phosphite reduction of 2-nitrosobiphenyl to carbazole in triethyl phosphate as solvent is of the first order in both reactants; the activation energy is 11·56 kcal. mole–1, and the entropy of activation ΔS*, at 25° is –29 e.u. The similarity of these data to those obtained for the Menshutkin and Arbusov reactions indicates that the rate-determining step involves the formation of an intermediate complex involving both reagents, possibly (EtO)3P+–O––NAr, which then decomposes rapidly to give products. The possible intermediacy of a nitrene is neither proved or disproved.Keywords
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