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- W1662206987 abstract "Aromatization of indolines is important in completing synthetic sequences, in which the directive effects of the indoline ring have been used to achieve selective carbocyclic substitution. One type of procedure represents use of oxidants, which are known to convert amines to imines. Aromatization then provides the indole. Such reagents must not subsequently oxidize the indole. Mercuric acetate (Entry 1) is known to oxidize other types of amines and presumably reacts by an oxidative deprotonation at α- to the complexed nitrogen. 3-Acyl groups on the indole ring can generally be reduced directly to 3-alkyl groups. The reduction proceeds through the intermediate indol-3-ylcarbinol stage and carbinols prepared by other means are also susceptible to reductive deoxygenation. The facility of these reductive displacements depends upon the susceptibility of indol-3-ylcarbinols to elimination. The conversion of indoles to oxindoles can be achieved in several ways. Reaction of indoles with a halogenating agent such as NCS, NBS or pyridinium bromide perbromide in hydroxylic solvents leads to oxindoles. The reaction proceeds by nucleophilic addition to a 3-haloindolenium intermediate." @default.
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- W1662206987 date "1996-01-01" @default.
- W1662206987 modified "2023-10-16" @default.
- W1662206987 title "Selective Reduction and Oxidation Reactions" @default.
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- W1662206987 doi "https://doi.org/10.1016/b978-012676945-6/50035-1" @default.
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