Effective Aromaticity of Tricarbonylchromiumbenzene, about 25 Enhanced over that of Benzene:  Structural Evidence from a Complexed Benzannulene

Abstract

The tricarbonylchromium complex of 2,7-di-tert-butyl-trans-12c,12d-dimethylbenzo[e]dihydropyrene is prepared in 65% yield from the parent annulene. Analysis of the (1)H NMR spectrum leads to coupling constant data and Günther's "Q" value data which unequivocally indicate that the tricarbonylchromiumbenzene moiety behaves like an aromatic system of greater bond fixing ability, aromaticity, than benzene itself; this analysis is supported by X-ray structural data and by the rotational position of the tricarbonyl podal. Analysis of chemical shift data indicates that the tricarbonylchromium benzene moiety has about 25% enhanced "aromaticity" over that of benzene.