Hypervalent iodine oxidation of amines using iodosobenzene: Synthesis of nitriles, ketones and lactams

Robert M Moriarty, Radhe K Vaid, Michael P Duncan, Masahito Ochiai, Minako Inenaga, Yoshimitsu Nagao*

doi:10.1016/s0040-4039(00)88473-7

Hypervalent iodine oxidation of amines using iodosobenzene: Synthesis of nitriles, ketones and lactams

DOI Web Site Web Site 被引用文献8件

書誌事項

公開日: 1988-01

権利情報

https://www.elsevier.com/tdm/userlicense/1.0/

DOI

10.1016/s0040-4039(00)88473-7

公開者: Elsevier BV

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説明

Abstract Primary aliphatic amines on oxidation with iodosobenzene in CH2Cl2 or H2O yield the corresponding nitriles, while primary cycloalkylamines give the corresponding cyclic ketones. Lactams are obtained by the oxidation of cyclic amines. (S)(−) Nicotine ( 15 ) is oxidized to ( + )-cotinine ( 16 ). The intermediary imine involved in these processes was trapped in the case of piperidine as the α-aminonitrile.