The oxidation of hexahelicenes. Synthesis of hexahelicene‐5,6‐quinone

作者: J. W. Diesveld , J. H. Borkent , W. H. Laarhoven

DOI: 10.1002/RECL.19800991205

关键词:

摘要: The remarkable ease with which 1,3,14,16-tetramethylhexahelicene can be oxidised has to ascribed the electronic effect of multiple methyl substitution and not disturbance helical conformation, as might concluded from polarographic oxidation potentials hexahelicene some its derivatives. Oxidation chromic acid in acetic gives hexahelicene-5,6-quinone 70% yield. Its structure was proven by spectroscopic methods.

参考文章(10)
J.H. Borkent, W.H. Laarhoven, The thermal racemization of methyl-substituted hexahelicenes Tetrahedron. ,vol. 34, pp. 2565- 2567 ,(1978) , 10.1016/0040-4020(78)88387-2
R.H. Martin, N. Defay, H.P. Figeys, M. Flammang-Barbieux, J.P. Cosyn, M. Gelbcke, J.J. Schurter, Studies in NMR spectroscopy: The helicenes and lower benzologues☆☆☆★ Tetrahedron. ,vol. 25, pp. 4985- 4998 ,(1969) , 10.1016/S0040-4020(01)83246-4
E. S. Pysh, N. C. Yang, Polarographic Oxidation Potentials of Aromatic Compounds Journal of the American Chemical Society. ,vol. 85, pp. 2124- 2130 ,(1963) , 10.1021/JA00897A019
P. M. op den Brouw, W. H. Laarhoven, Addition and substitution reactions of hexahelicene: Bromination, nitration and acetylation Recueil des Travaux Chimiques des Pays-Bas. ,vol. 97, pp. 265- 268 ,(1978) , 10.1002/RECL.19780971007
J. B. M. Somers, W. H. Laarhoven, Conformational equilibria of 3‐(cis‐styryl)phenanthrene and some benzologues Recueil des Travaux Chimiques des Pays-Bas. ,vol. 99, pp. 160- 166 ,(2010) , 10.1002/RECL.19800990504
K.D. Bartle, J.A.S. Smith, High-resolution nuclear magnetic resonance spectra of phenanthrenes—II Halogeno-, cyano-, nitro- and carbonyl phenanthrenes, and phenanthrene-9,10-quinone Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 23, pp. 1715- 1734 ,(1967) , 10.1016/0584-8539(67)80054-0
W. H. Laarhoven, G. J. M. Brus, Polarographic data and deviations from coplanarity of helicene molecules Journal of The Chemical Society B: Physical Organic. ,vol. 1971, pp. 1433- 1434 ,(1971) , 10.1039/J29710001433
W.H. Laarhoven, Th.J.H.M. Cuppen, Conformational studies on hexahelicenes—III Tetrahedron. ,vol. 30, pp. 1101- 1106 ,(1972) , 10.1016/S0040-4020(01)97275-8
Sigrid Obenland, W. Schmidt, Photoelectron spectra of polynuclear aromatics. IV. Helicenes Journal of the American Chemical Society. ,vol. 97, pp. 6633- 6638 ,(1975) , 10.1021/JA00856A006