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Conformational study on indoline compounds. Structures of 2‐phenyl‐3‐arylimino‐3 H ‐indole 1‐Oxide, 1,2‐dihydro‐2‐phenyl‐2‐benzyl‐ and 2‐ tert ‐Butyl‐3‐phenylimino‐3 H ‐indole 1‐oxyls
Author(s) -
Rizzoli Corrado,
Sgarabotto Paolo,
Ugozzoli Franco,
Carloni Patricia,
Damiani Elisabetta,
Greci Lucedio,
Stipa Pierluigi
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300310
Subject(s) - chemistry , nitrosobenzene , diastereomer , indoline , indole test , crystal structure , nitrone , medicinal chemistry , stereospecificity , oxide , stereochemistry , cycloaddition , organic chemistry , catalysis
Reacting 1‐hydroxy‐2‐phenylindole with nitrosobenzene, 2‐phenyl‐3‐phenylimino‐3 H ‐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.