- Hypervalent iodine catalyzed hofmann rearrangement of carboxamides using oxone as terminal oxidant
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Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene. This reaction involves hypervalent iodine species generated in situ from catalytic amount of PhI and Oxone in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) in aqueous methanol solutions. Under these conditions, Hofmann rearrangement of various carboxamides affords corresponding carbamates in high yields.
- Yoshimura, Akira,Middleton, Kyle R.,Luedtke, Matthew W.,Zhu, Chenjie,Zhdankin, Viktor V.
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p. 11399 - 11404
(2013/02/23)
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- Alkylwanderungen bei Sextettumlagerungen
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The migration aptitude of alkyl groups in the Beckmann-, the Criegee-, and the isonitrile-nitrile rearrangements were investigated.The relative rearrangement rates of substituted benzyl groups are an expression of the charge on the migrating carbon at transition state.From the relative rates of migration of exo- and endo-2-norbornyl groups the geometrical changes at the migrating carbon is estimated.Finally, the different influence of α-branching in the migrating group is discussed for these and some other rearrangements.
- Langhals, Heinz,Range, Guenter,Wistuba, Eckehardt,Ruechardt, Christoph
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p. 3813 - 3830
(2007/10/02)
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