Radical cations of 1,2-bis(dialkylamino)benzenes: Restricted rotation about the 
C-NMe2 bond

Neugebauer, Franz A.; Funk, Britta; Staab, Heinz A.

doi:10.1016/S0040-4039(00)76959-0

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Radical cations of 1,2-bis(dialkylamino)benzenes: Restricted rotation about the C-NMe2 bond

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

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Staab, Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Neugebauer, F. A., Funk, B., & Staab, H. A. (1994). Radical cations of 1,2-bis(dialkylamino)benzenes: Restricted rotation about the C-NMe2 bond. Tetrahedron Letters, 35(27), 4755-4758. doi:10.1016/S0040-4039(00)76959-0.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-A8F0-0

Abstract

The 1,2-bis(dialkylamino)benzene radical cations 2a–c⊎+ were generated by oxidation of the parent compounds with iodine or lead tetraacetate. ESR and ENDOR studies of 2a⊎+ and 2b⊎+ gave evidence of a restricted rotation about the CNMe2 bond; based on the results of 2c⊎+ the different N-methyl proton splittings in 2a⊎+ and 2b⊎+ were assigned to the exo and endo N-methyl groups. ESR of the radical cations 2a–c???+; restricted rotation about the C(aryl)N bond; endo/exo assignment of the N-methyl groups.