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N,N-bridged 1,4,5,8-tetrakis(methylamino)naphthalenes and their radical cations. Comparison with 1,4,5,8-tetrakis(dimethylamino)naphthalene and related radical cations

MPG-Autoren
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Barth,  Thomas
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Zitation

Barth, T., & Neugebauer, F. A. (1995). N,N-bridged 1,4,5,8-tetrakis(methylamino)naphthalenes and their radical cations. Comparison with 1,4,5,8-tetrakis(dimethylamino)naphthalene and related radical cations. Journal of Organic Chemistry, 60(17), 5401-5406. doi:10.1021/jo00122a015.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-002B-41DE-A
Zusammenfassung
Syntheses of 3,8-dihydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidine-2,7-1H,6H)-dione (2), 1,2,3,6,7,8-hexahydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidine (3), and 3,6,7,8-tetrahydro-1,3,6,8-tetramethylpyrimido[4,5,6-gh]perimidin-2(1H)-one (4) are reported. The corresponding radical cations were generated by oxidation with iodine or tris(4-bromophenyl)amminium hexachlo-roantimonate and were studied by ESR and ENDOR for comparison with the 1,4,5,8-tetrakis-(dimethylamino)naphthalene radical cation (1.+). The ESR results of 2.+-4.+, however, give no indications which could explain the widely different exo (3.54 G) and endo (1.77 G) N-methyl proton splittings in 1.+.