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Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles
Author(s) -
Xu Jiaxi,
Gao Yu,
Li Zhenjiang,
Liu Jingjing,
Guo Tianfo,
Zhang Lei,
Wang Haixin,
Zhang Zhihao,
Guo Kai
Publication year - 2020
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.201901537
Subject(s) - chemistry , beckmann rearrangement , nitrile , oxime , amide , ether , organic chemistry , catalysis , chloride , medicinal chemistry
Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.