The Combination of TsNH 2  and NCS as Nitrogen and Chlorine Sources for Direct Diamination of Enones | Zendy

Timmons Cody | Zendy; Chen Dianjun | Zendy; Xu Xin | Zendy; Li Guigen | Zendy

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The Combination of TsNH 2 and NCS as Nitrogen and Chlorine Sources for Direct Diamination of Enones

Author(s) -

Timmons Cody,

Chen Dianjun,

Xu Xin,

Li Guigen

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300326

Subject(s) - chemistry , electrophile , nucleophile , nitrogen , ring (chemistry) , chlorine , regioselectivity , combinatorial chemistry , amination , chlorine atom , medicinal chemistry , organic chemistry , catalysis

The regio‐, stereo‐, and chemoselective diamination of enones has been achieved without the observation of any haloamines. The reaction employs the readily available inexpensive combination of NCS and TsNH 2 as an electrophilic nitrogen source, and three nitriles as nucleophilic nitrogen sources. A novel mechanism involving the formation of aziridinium intermediates from the reaction of TsNHCl with olefins and a new [2+3] cyclic addition for aziridinim ring opening has been proposed for the electrophilic diamination of olefins. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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