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

descriptionPublicationkeyboard_double_arrow_right Article 01 Jul 1971 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 24, pages 1,425-1,436 (issn: 0004-9425, eissn: 1445-0038,

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Authors: JR Campbell; A Pross; S Sternhell;

doi: 10.1071/ch9711425

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

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Abstract

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.

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