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 spectroscopy and X-ray crystal structure and represents an unexpected stereospecific reaction.
Conformational Study on Indoline Compounds. Structures of 2-phenyl-3-arylimino-3H-indole 1-oxide, 1,2-dihydro-2-phenyl-2-benzyl- and 2-tert-Butyl-3-phenylimino-3H-indole 1-oxyls / C., Rizzoli; P., Sgarabotto; F., Ugozzoli; Carloni, Patricia; Damiani, Elisabetta; L., Greci; Stipa, Pierluigi. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 30:(1993), pp. 637-642.
Conformational Study on Indoline Compounds. Structures of 2-phenyl-3-arylimino-3H-indole 1-oxide, 1,2-dihydro-2-phenyl-2-benzyl- and 2-tert-Butyl-3-phenylimino-3H-indole 1-oxyls
CARLONI, PATRICIA;DAMIANI, Elisabetta;STIPA, Pierluigi
1993-01-01
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 spectroscopy and X-ray crystal structure and represents an unexpected stereospecific reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
