Synthesis of dicyclopenta [ef, kl] heptalene (azupyrene). II. Routes from 1, 6, 7, 8, 9, 9a-hexahydro-2H-benzo [c, d] azulen-6-one and 5-phenylpentanoic acid

AG Anderson Jr, AF Montana…

Index: Anderson,A.G. et al. Journal of Organic Chemistry, 1973 , vol. 38, # 8 p. 1445 - 1450

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Citation Number: 18

Abstract

3 4 dehydration of 2:(i) treatment with thionyl chloride and pyridine (84%);(ii) refluxing with p- toluenesulfonic acid in toluene (93%); and (iii) heating with anhydrous formic acid (97.5%). The infrared (two carbonyl peaks) and the nuclear magnetic resonance (vinylic singlet superimposed on a triplet) spectra of the dehydration product showed the presence of two species (8 and 9, Scheme II).'Hydrogenation of the