Issue 0, 1984

Polyhalogenoheterocyclic compounds. Part 36. Additions of diazomethane to perfluoropolyalkylethenes. A frontier orbital rationalisation of reactions of fluorinated alkenes with 1,3-dipoles and nucleophiles

Abstract

Additions of diazomethane to fluorinated alkenes have established the reactivity order (RF)2C[double bond, length half m-dash]C(RF)2 > (RF)2C[double bond, length half m-dash]CFRF [double greater-than, compressed](RF)2C[double bond, length half m-dash]CF2, RFCF[double bond, length half m-dash]CFRF(RF= perfluoroalkyl). Highly regioselective addition occurs with the carbon of the dipole becoming attached preferentially to the site in the alkene most susceptible to nucleophilic attack. An approach based on considering frontier orbitals (F.O.) leads to a model for reactivity towards diazomethane in these systems. Also, consideration of F.O. is suggested as an alternative approach to accounting for reactions involving nucleophilic attack on fluorinated alkenes.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 509-514

Polyhalogenoheterocyclic compounds. Part 36. Additions of diazomethane to perfluoropolyalkylethenes. A frontier orbital rationalisation of reactions of fluorinated alkenes with 1,3-dipoles and nucleophiles

M. R. Bryce, R. D. Chambers and G. Taylor, J. Chem. Soc., Perkin Trans. 1, 1984, 509 DOI: 10.1039/P19840000509

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