Novel reactions of indolenines
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 1667-1675
- https://doi.org/10.1039/j39680001667
Abstract
3,3-Disubstituted indolenines readily undergo addition by Grignard reagents to afford 2,3,3-trisubstituted indolines; the reaction is stereospecific if one of the 3-substituents is considerably larger than the other. The diastereoisomeric indolines may be obtained by hydrogenation of the appropriate 2,3,3-trisubstituted indolenines. 2,3,3-Trialkylindolenines are alkylated by Grignard reagents at the α-methylene group of the 2-alkyl substituent. Such indolenines easily autoxidise, e.g., 2-ethyl-3,3-dimethylindolenine affords 2-acetyl-3,3-dimethylindolenine. Mass and n.m.r. spectra of most of the indolenines and indolines are recorded.Keywords
This publication has 0 references indexed in Scilit: