Attempted Synthesis of Bowl-Shaped Polycyclic Aromatic Hydrocarbons via Oxidative Electrocyclization. Products from the Dications of Dibenzo [g, p] chrysene, Tetrabenzo[5.5]fulvalene, and Diphenylmethylidenefluorene

Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C 60 surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF 5 /SO 2 CIF. Compounds 2 and 3 were oxidized to dications...

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Bibliographic Details
Published in:	Polycyclic aromatic compounds Vol. 12; no. 4; pp. 239 - 247
Main Authors:	Mills, Nancy S., Malandra, James L., Hensen, Antoinette, Lowery, John A.
Format:	Journal Article
Language:	English
Published:	Taylor & Francis Group 01-04-1998
Subjects:	Bowl-shaped polycyclic aromatic hydrocarbons dications diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene
Online Access:	Get full text
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Summary:	Synthesis of diindeno[1,2,3,4-defg: 1′,2′,3′,4′-mnop]chrysene (1), a portion of the C 60 surface, was attempted through oxidative cyclization of tetrabenzo[5.5]fulvalene (2), dibenzo[gp]chrysene (3), and diphenylmethylidenefluorene (4) by SbF 5 /SO 2 CIF. Compounds 2 and 3 were oxidized to dications which then underwent a single cyclization to give precursors to 1. Compound 4 underwent two oxidative cyclizations to give a precursor to 1. AM1 calculations of the possible products from cyclization were consistent with preferential formation of the cyclized product with the lower ΔHf. Oxidative cyclization may offer a one-pot synthetic alternative for the preparation of unusual polycyclic aromatic hydrocarbons.
ISSN:	1040-6638 1563-5333
DOI:	10.1080/10406639808233841