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

• Published in: Journal of heterocyclic chemistry Vol. 30; no. 3; pp. 637 - 642
• Main Authors: Rizzoli, Corrado, Sgarabotto, Paolo, Ugozzoli, Franco, Carloni, Patricia, Damiani, Elisabetta, Greci, Lucedio, Stipa, Pierluigi
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley-Blackwell 01-05-1993; Wiley‐Blackwell; HeteroCorporation
• Subjects: Chemistry; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Organic compounds; Physics; Preparations and properties; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Nitroxyl; Molecular structure; Nitrogen heterocycle; Organic free radical; Nitrone; Bicyclic compound; Ketimine; Aromatic compound; Experimental study; X ray diffraction; Crystalline structure
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570300310

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.