Preparation and chemistry of some 1-iodo-1-phenylpropenes

J. R. Campbell, A. Pross, S. Sternhell

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73% and 19-43% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp2-hybridized ("bent") 1-arylpropenyl radical.

Original languageEnglish
Pages (from-to)1425-1436
Number of pages12
JournalAustralian Journal of Chemistry
Issue number7
StatePublished - 1 Jan 1971
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry (all)


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