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Dimethyldihydropyrene−Dehydrobenzoannulene Hybrids: Studies in Aromaticity and Photoisomerization

2002; American Chemical Society; Volume: 67; Issue: 25 Linguagem: Inglês

10.1021/jo020462q

1520-6904

David B. Kimball, Michael M. Haley, Reginald H. Mitchell, Timothy R. Ward, Subhajit Bandyopadhyay, Richard Vaughan Williams, John R. Armantrout,

Organic Chemistry Cycloaddition Reactions

The synthesis and study of dehydrobenzoannulene (DBA)-dimethyldihydropyrene (DDP) hybrids as models for the investigation of aromaticity in weakly diatropic systems is reported. Three new monofused DBA-DDP hybrids have been synthesized, and their NMR spectra are discussed with regard to quantifying the aromaticity remaining in multibenzene-fused DBAs. Nucleus-independent chemical shifts, determined at a series of locations for each compound, bond lengths, and (1)H and (13)C NMR chemical shifts were calculated and used to probe the aromaticity of these hybrids. Systems where more than one annulene/DBA is fused to the DDP core have also been obtained, and their potential use in photoinduced isomerization applications is discussed.