1,2,5,6-TETRAKETOPYRACENE - SYNTHESIS, AND STRUCTURE BY AB-INITIO CALCULATION AND X-RAY-ANALYSIS

Authors
ABDOURAZAK AH MARCINOW Z FOLSOM HE FRONCZEK FR SYGULA R SYGULA A RABIDEAU PW
Citation
Ah. Abdourazak et al., 1,2,5,6-TETRAKETOPYRACENE - SYNTHESIS, AND STRUCTURE BY AB-INITIO CALCULATION AND X-RAY-ANALYSIS, Tetrahedron letters, 35(23), 1994, pp. 3857-3860
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
23
Year of publication
1994
Pages
3857 - 3860
Database
ISI
SICI code
0040-4039(1994)35:23<3857:1-SASB>2.0.ZU;2-L
Abstract
The title compound is conveniently synthesized from the known 1,2-dike topyracene via NBS bromination followed by reaction with silver nitrat e in acetonitrile, and treatment with sodium acetate trihydrate in DMS O. Ifs structure determined by semiempiricnl PM3 and ab initio calcula tions is in excellent agreement with the x-ray analysis, and suggests that the bond alternation observed in pyracylene and related compounds is probably not due to antiaromaticity.