Synthesis of Dibenzopyrenes and Pyrenes via Photolytic Sulfur Extrusion and Intramolecular Cross-Coupling Reactions of Dithia[3.3](1,3)naphthalenophanes and Dithia[3.3]metacyclophanes
journal contributionposted on 19.09.1997, 00:00 by Muhammad Ashram, David O. Miller, John N. Bridson, Paris E. Georghiou
The syntheses of several substituted dithia[3.3]metacyclophanes and dithia[3.3](1,3)naphthalenophanes are reported and their photolyses in triethyl or trimethyl phosphite are described. Under these conditions, the corresponding tetrahydrodibenzopyrenes and tetrahydropyrenes are produced in a one-pot procedure when the precursor dithianaphthalenophanes and dithiacyclophanes possess at least one intraannular methoxyl group. A mechanism with supporting evidence is proposed to account for these results. Structural determinations of the four isomeric 11,22-dimethoxy-2,13-dithia[3.3](1,3)naphthalenophanes by NMR and X-ray single-crystal diffraction studies are also described. The syntheses of the novel anti-transoid- and anti-cisoid-[2.2](1,3)naphthalenophanes are also described.
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trimethyl phosphiteStructural determinationsevidencecisoidisomericphotolysedithiacyclophanetetrahydropyreneprecursor dithianaphthalenophanesmechanismtriethyldimethoxySynthesiPhotolytic Sulfur ExtrusionDibenzopyrenetransoidsyntheseDithiaNMRtetrahydrodibenzopyreneintraannular methoxyl groupdiffractionIntramolecularPyreneprocedure