Nitrogen configuration determined by X-ray analysis on an homogeneous series of 3-Indolinones

• Published in: Journal of heterocyclic chemistry Vol. 33; no. 1; pp. 81 - 85
• Main Authors: Carloni, Patricia, Greci, Lucedio, Stipa, Pierluigi, Cauzzi, Daniele, Rizzoli, Corrado, Sgarabotto, Paolo
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley-Blackwell 01-01-1996; Wiley‐Blackwell
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570330114

The X‐ray diffraction analyses of 2‐methyl‐2‐phenylindolin‐3‐one 1, 1,2‐dimethyl‐2‐phenylindolin‐3‐one 2, 1‐hydroxy‐2‐methyl‐2‐phenylindolin‐3‐one 3 and 1‐methoxy‐2‐methyl‐2‐phenylindolin‐3‐one 4 have been carried out and the structural data were compared with those of 1‐oxyl‐2‐methyl‐2‐phenylindolin‐3‐one 5. The results demonstrate that only compounds 2 and 5 show planar trigonal geometry which is coplanar with the conjugated benzene ring of the indolinic nucleus, whereas compounds 3 and 4 show a marked pyramidality of the nitrogen. Even if compound 1 shows a certain pyramidality of the nitrogen, it has been considered similar to compound 2. The reactivity of all studied compounds fit the structural data.