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

The chemistry of pyrrolic compounds. XL. A new synthesis of protoporphyrins III and XIII and a 1H N.M.R. study of the preferred pathway of electron delocalization in the porphyrin macrocycle

PS Clezy, CJR Fookes and S Sternhell

Australian Journal of Chemistry 31(3) 639 - 648
Published: 1978

Abstract

The synthesis of protoporphyrins III and XIII as the dimethyl esters has been completed by an oxidative cyclization of biladiene-ac intermediates. Protoporphyrin III has been converted into deuteroporphyrin III and measurements of the proton coupling constant in the allylic unit, CH3-C=C-H, of this latter porphyrin point to the double bond of this system having a significantly diminished bond order. This finding is in accord with the view that the π-electron delocalization pathway in the porphyrin macrocycle involves the periphery of the molecule.

https://doi.org/10.1071/CH9780639

© CSIRO 1978

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