Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride

Journal Article (Journal Article)

Grignard reagents from N-unsubstituted indoles and benzenesulfonyl chloride undergo reaction such as to produce unstable intermediates of β-chlorination and a-sulfonylation, which are transformed into oxindoles or substituted indoles. In the same reaction, yuehchukene (the naturally occurring dehydroprenylindole dimer) is converted into a spirooxindole, containing a strained four-membered ring, which is changed into a spirooxindole isomer with ring expansion on mild acid treatment. © 1987, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Wenkert, E; Moeller, PDR; Piettre, SR; McPhail, AT

Published Date

  • July 1, 1987

Published In

Volume / Issue

  • 52 / 15

Start / End Page

  • 3404 - 3409

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00391a044

Citation Source

  • Scopus