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- W1984676543 abstract "Second-order rate coefficients and activation parameters are reported for the reaction in solution of triphenylphosphine with a series of diazoalkanes (Ar2CN2) having two aromatic groups attached to the diazo-carbon atom, 9-diazofluorene (DAF), 5-diazo-5H-dibenzo[a,d]cycloheptene (DBSE), its 10,11-dihydro analogue (DBSA), and diazodiphenylmethane (DDM). Although the product phosphazine Ar2CNNPPh3 arises formally by nucleophilic attack of phosphorus on the terminal nitrogen atom of the diazoalkane, the pattern of reactivity approximates to that for proton transfer from acetic acid to the diazoalkane under similar conditions, highlighting the biphilic nature of the reaction. The results can be rationalised in terms of qualitative FMO theory taking into account both HOMO(Ph3P)–LUMO (Ar2CN2) and HOMO(Ar2CN2)–LUMO (Ph3P) interactions. This is lent qualified support by MNDO calculations on Ar2CN2 based on molecular parameters from the X-ray crystal structure of DAF itself and of the ketones corresponding to DBSE, DBSA, and DDM." @default.
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- W1984676543 date "1989-01-01" @default.
- W1984676543 modified "2023-09-26" @default.
- W1984676543 title "A kinetic study of the reaction of diazoalkanes with triphenylphosphine: structure and reactivity in a biphilic process" @default.
- W1984676543 doi "https://doi.org/10.1039/p29890001829" @default.
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