Undoubtedly, the unceasing interest in polypyrrole macrocycles is iustified by the central role which porphyrin derivatives (e.9. haemoglobin, cytochromes, chlorophylls, and, in a broader sense, vitamin B12 coenzyme) play in several essential biological processes. Thus, since Hans Flscher in 1929 proved the correctness of Kiister's cyclic tetrapyrrole structure of the porphvrin nucleus, phenomenal advances has been made in the understandinq of the physical and chemical properties of this class of compounds.') A further influence which fostered the development o f porphvrin chemistry has been the interest in the theoretical aspects of aromaticity such as the extend to which modification and expansion of cyclic systems of conjugated double bonds is possible while still retaining aromatic character. Of particular significance in this connection are pyrrole macrocycles with more than four rinqs whose spectroscopic and metal chelate forming properties should be dependent on ring size. Sapphyrins (e.g. 1) are the first example of this kind of compounds which was The present work deals with the first syntheses of two polypyrrole macrocycles analoqous to the porphyrins, i.e. havinq the same number of pyrrole rings and methine bridges. The five membered macrocycle 5 was obtained by condensation of the dipyrrvlmethane 3a with the dialdehyde 4a i n the presence of hydrobromic acid and subsequent oxidation o f the reaction mixture with chloranil. It is noteworthv that, under the same conditions, the condensationofthe diformvldipyrrylmethane 3b with the tripyrrane 4b yielded a porphyrin, instead of 5 as the product. In fact, the later approach has been found to be unsuccessful for synthesizing pentapvrrole macrocvcles by other authors also.5f6) 2 -7 9 3 -