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.
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 / Rizzoli, Corrado; Sgarabotto, Paolo; Ugozzoli, Franco; P., Carloni; E., Damiani; L., Greci; P., Stipa. - In: JOURNAL OF HETEROCYCLIC CHEMISTRY. - ISSN 0022-152X. - 30:(1993), pp. 637-642. [10.1002/jhet.5570300310]
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
RIZZOLI, Corrado;SGARABOTTO, Paolo;UGOZZOLI, Franco;
1993-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
