Tetrahedron

Non-kekulé molecules derived conceptually by heteroatom-for-carbon substitution in alternant hydrocarbons: M-Quinomethane and M-Naphthoquinomethane

…, DE Seeger, EF Hilinski, DA Dougherty, JA Berson

Index: Rule, Mark; Matlin, Albert R.; Seeger, David E.; Hilinski, Edwin F.; Dougherty, Dennis A.; Berson, Jerome A. Tetrahedron, 1982 , vol. 38, # 6 p. 787 - 798

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Citation Number: 64

Abstract

Qualitative theoretical consideration suggest that substitution of a heteroatom for a C atom in an alternant hydrocarbon might results in a non-Kekulé with a triplet ground state, despite the nondegeneracy of the Hückel MBMOs of the heteroatom derivatives. The syntheses of 3- methylene-1-phenoxyl and 3-methylene-1-naphthoxyl are described. These compounds. biradical valence tautomers of m-quinomethanes, are characterized by EPR spectroscopy ...