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

โœ Scribed by Robert M Moriarty; Radhe K Vaid; Michael P Duncan; Masahito Ochiai; Minako Inenaga; Yoshimitsu Nagao*

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
256 KB
Volume
29
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Primary aliphatic amines on oxidation with iodosobenzene in CH2C12 or H20 yield the corresponding nitriles, while primary cycloalkylamines give the corresponding cyclic ketones. Lactams are obtained by the oxidation of cyclic amines. (S)(-) Nicotine (JJ,) is oxidized to (+)-cotinine (a).

The intermediary imine involved in these processes was trapped in the case of piperidine as the a-aminonitrile.

๐Ÿ“œ SIMILAR VOLUMES

Hypervalent iodine oxidation: Synthesis
Hypervalent iodine oxidation: Synthesis of 5-substituted-2(5H)-furanones using iodosobenzene
โœ Robert M. Moriarty; Radhe K. Vaid; Thomas E. Hopkins; Beena K. Vaid; Atilla Tunc ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 254 KB

Hypervalent iodine oxidation of Z-(trimethylsilyloxy)furan with iodosobenzeneboron bifluoride etherate in the presence of various nucleophiles yields 5-substituted-2(.5H)-furanones. 5Substituted-2(5H)-furanones are versatile intermediates for the synthesis of a number of important natural products a