Formation of monohomocyclooctatetraene dianions in liquid ammonia. Analysis of the nucleophilic reactivity of the cyclononatrienyl anions generated upon solvent …

LA Paquette, SV Ley, SG Traynor…

Index: Paquette,L.A. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 8162 - 8172

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Citation Number: 9

Abstract

Abstract: Reactions of the cyclononatrienyl anion (3) and its 8-methyl (20) and 8, 8-dimethyl (4) homologues, which are generated via in situ protonation by solvent ammonia of homocyclooctatetraene dianions, are shown to proceed at C (3) and C (5) which are the sites of highest electron density ('H NMR analysis). For the parent system, these sites are equivalent by symmetry, but this is not so for its congeners, and the question of ...