35341-35-6Relevant articles and documents
Sterically Congested Polycyclic Hydrocarbons with Nonoptimal Geometries. 4,5-Didehydroacenaphthene as a Precursor for the Synthesis of 7,14-Diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene
Plummer, Benjamin F.,Russell, Steven J.,Reese, W. Gregory,Watson, William H.,Krawiec, Mariusz
, p. 3219 - 3223 (2007/10/02)
A multistep synthetic route for the synthesis of the reactive intermediate 4,5-didehydroacenaphthene (15) is described.A mixture of N-1-, N-2-, and N-3-aminoacenaphthotriazoles is produced, which is oxidized by lead tetraacetate (LTA) to the corresponding aryne.The N-2-triazole is oxidized by LTA to 7-cyano-1-(cyanomethylene)indan (18), whose structure was verified by X-ray analysis.Intermediate 15 was trapped by 7,9-diphenyl-8H-cyclopentaacenaphthylen-8-one (acecyclone) to produce the congested hydrocarbon 7,14-diphenyl-8,9-(1',8'-naphthenylene)acephenanthrene (20).There is a small deviation from planarity for 20, and this is modeled by MMX calculations and verified by X-ray crystallographic analysis of the structure.