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Lutz, Toni A.; Spanner, Patrick; Wanner, Klaus T. (2016): A general approach to substituted diphenyldiazenes. In: Tetrahedron, Vol. 72, No. 12: pp. 1579-1589
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A general and practical synthetic method for the construction of unsymmetrically substituted diphenyldiazenes based on classical azo coupling reaction has been developed. A key feature of this method is the use of N,N-diallyl protected aniline derivatives as coupling components. The N,N-diallyl moiety of the coupling component warrants sufficient reactivity and allows to avoid formation of constitutional isomers resulting from intermediate triazene formation. Furthermore, subsequent to the coupling reaction, the N,N-diallyl aminofunction, can be replaced by other substituents including hydrogen via diazonium ion intermediates. In general, following this approach target compounds can be obtained in reasonable to good yields. (C) 2016 Elsevier Ltd. All rights reserved.