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

Authors
RIZZOLI C SGARABOTTO P UGOZZOLI F CARLONI P DAMIANI E GRECI L STIPA P
Citation
C. Rizzoli et al., 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, Journal of heterocyclic chemistry, 30(3), 1993, pp. 637-642
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
30
Issue
3
Year of publication
1993
Pages
637 - 642
Database
ISI
SICI code
0022-152X(1993)30:3<637:CSOIC->2.0.ZU;2-6
Abstract
Reacting 1-hydroxy-2-phenylindole with nitrosobenzene, 2-phenyl-3-phen ylimino-3H-indole 1-oxide (1) is produced in only one of the two possi ble diastereomers. The latter reacts with tert-butylmagnesium chloride and benzylmagnesium chloride giving, after oxidation, the correspondi ng aminoxyls which show the same configuration of the phenylimino grou p at C-3 as in 1. This has been demonstrated by means of nmr spectrosc opy and X-ray crystal structure and represents an unexpected stereospe cific reaction.