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2,2‐Diazido‐1,2‐diarylethanones: Synthesis and Reactivity with Primary Amines
Author(s) -
Holzschneider Kristina,
Häring Andreas P.,
Kirsch Stefan F.
Publication year - 2019
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.201900292
Subject(s) - chemistry , reactivity (psychology) , amine gas treating , azide , nucleophile , fragmentation (computing) , sodium azide , primary (astronomy) , organic chemistry , combinatorial chemistry , catalysis , medicine , physics , alternative medicine , pathology , astronomy , computer science , operating system
We describe the synthesis and reactivity of a new class of diazidated compounds: the 2,2‐diazido‐1,2‐diarylethanones. The diazides are easily accessible from 1,2‐diarylethanones through a mild and simple protocol for the direct oxidative diazidation, using iodine and sodium azide in DMSO at room temperature. In studies towards their reactivity with amine nucleophiles under basic conditions, the diazides are shown to undergo a controlled fragmentation reaction that provides a straightforward access to the corresponding amides. In stark contrast to our previous results on the amine‐triggered fragmentation of diazidated compounds, aromatic nitriles are found to be by‐products of synthetic value. The net reaction consisting of diazidation and subsequent fragmentation, thus, provides a simple way to convert 1,2‐diarylethanones into both aromatic amides and nitriles.