Generation and ring-opening of 2,3-dilithio-1-(phenylsulfonyl)indole
β Scribed by Gribble, Gordon W.; Saulnier, Mark G.
- Book ID
- 126047466
- Publisher
- American Chemical Society
- Year
- 1983
- Tongue
- English
- Weight
- 463 KB
- Volume
- 48
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Generation of 2,3-dilithio-N-methylindole (7) from 2,3-diiodo-N-methylindole ( 6) and subsequent reaction with various electrophiles (NH 4 Cl, DMF, ClCO 2 Me, CO 2 , phthalic anhydride) affords the corresponding 2,3-disubstituted indoles in good to excellent yields (41-99%).
Reaction of 1-indolylmagnesium iodidelo with the appropriate sulfonyldiene in benzene-ether (1: 1) at 0 "C resulted in a cycloaddition and after workup the teaahydrocarbazole product was isolated. Results from the reaction of a few 2-phenylsulfonyl 1,3-dienes are given in Table 1. In all cases only