Conformational study on indoline compounds. Structures of 2-phenyl-3-arylimino-3 H -indole 1-Oxide, 1,2-dihydro-2-phenyl-2-benzyl- and 2- tert -Butyl-3-phenylimino-3 H -indole 1-oxyls (original) (raw)

J Heterocycl Chem, 1993

Abstract

ABSTRACT Reacting 1-hydroxy-2-phenylindole with nitrosobenzene, 2-phenyl-3-phenylimino-3H-indole 1-oxide (1) is produced in only one of the two possible diastereomers. The latter reacts with tert-butylmagnesium chloride and benzylmagnesium chloride giving, after oxidation, the corresponding aminoxyls which show the same configuration of the phenylimino group at C-3 as in 1. This has been demonstrated by means of nmr spectros-copy and X-ray crystal structure and represents an unexpected stereospecific reaction.

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