A convergent route to structures with multiple contiguous carbon–nitrogen bonds. The divergent role of N -acyl groups

Songzhe Han; Samir Zard

doi:10.1016/j.tet.2016.05.085

Journal articles

A convergent route to structures with multiple contiguous carbon–nitrogen bonds. The divergent role of N -acyl groups

Songzhe Han ¹ Samir Zard ^{1, *}

* Corresponding author

1 DCSO - Laboratoire de synthèse organique

Abstract : The radical addition of xanthates to N,N-diacetyl imidazol-2-one can be followed by a second addition to N,N-di-Boc imidazol-2-one to give after reductive dexanthylation a protected tetra-amine possessing four contiguous carbon–nitrogen bonds, or even five if the starting xanthate itself bears a protected amine. The success of this sequence hinges on the difference in radical stability between radicals substituted by an N-acyl and N-carbamoyl nitrogens, which allows control of the radical addition and prevents the formation of oligomers.

Keywords : Radical addition Xanthates Tetra-amines Imidazolinones

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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A convergent route to structures with multiple contiguous carbon–nitrogen bonds. The divergent role of N -acyl groups

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A convergent route to structures with multiple contiguous carbon–nitrogen bonds. The divergent role of N -acyl groups

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