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Steric effects in the hypervalent iodine oxidation of ketones

โœ Scribed by Robert M. Moriarty; Indra Prakash; H.A. Musallam


Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
183 KB
Volume
25
Category
Article
ISSN
0040-4039

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Hypervalent iodine oxidation of amines u
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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 interm

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a-Trifluoromethanesulfonoxy ketones (a-keto triflates) have been synthesized under very mild conditions by the reaction of silyl enol ethers of ketones and nimethylsilyl trifluormethanesulfonate/iodosobenzene in dichloromethane.