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Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride

Publication ,  Journal Article
Wenkert, E; Moeller, PDR; Piettre, SR; McPhail, AT
Published in: Journal of Organic Chemistry
July 1, 1987

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.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

July 1, 1987

Volume

52

Issue

15

Start / End Page

3404 / 3409

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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MLA
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Wenkert, E., Moeller, P. D. R., Piettre, S. R., & McPhail, A. T. (1987). Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride. Journal of Organic Chemistry, 52(15), 3404–3409. https://doi.org/10.1021/jo00391a044
Wenkert, E., P. D. R. Moeller, S. R. Piettre, and A. T. McPhail. “Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride.” Journal of Organic Chemistry 52, no. 15 (July 1, 1987): 3404–9. https://doi.org/10.1021/jo00391a044.
Wenkert E, Moeller PDR, Piettre SR, McPhail AT. Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride. Journal of Organic Chemistry. 1987 Jul 1;52(15):3404–9.
Wenkert, E., et al. “Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride.” Journal of Organic Chemistry, vol. 52, no. 15, July 1987, pp. 3404–09. Scopus, doi:10.1021/jo00391a044.
Wenkert E, Moeller PDR, Piettre SR, McPhail AT. Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride. Journal of Organic Chemistry. 1987 Jul 1;52(15):3404–3409.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

July 1, 1987

Volume

52

Issue

15

Start / End Page

3404 / 3409

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry