Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Radical reactions of p-Nitrobenzylidene dichloride with lithium 2-nitropropan-2-ide. Consecutive SRN1 and ERC1 reactions

DJ Freeman and RK Norris

Australian Journal of Chemistry 29(12) 2631 - 2642
Published: 1976


The reaction of p-nitrobenzylidene dichloride with the lithium salt of 2-nitropropane gives initially the monosubstituted compound, p- NO2C6H4CH(Cl)CMe2NO2, by a radical-anion radical chain, SRN1 process. This compound then undergoes a radical-anion radical chain elimination reaction giving the styrene, p-NO2C6H4CH=CMe2, and the dimer of 2- nitropropane, Me2C(NO2)CMe2NO2. This latter reaction, which is designated ?ERC1?, also occurs in competition with an E2 reaction in the reaction of the methanesulphonate, p-NO2C6H4CH(OMs)CMe2NO2, with the 2- nitropropan-2-ide ion giving the above styrene and the enol methanesulphonate, p-NO2C6H4C(OMs)=CMe2, respectively. Catalytic, inhibition, and substituent effects are used to confirm the operation of these radical processes.

© CSIRO 1976

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