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Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide

Publication ,  Journal Article
Seltzman, HH; Moody, MA; Begum, MK
Published in: Tetrahedron Letters
June 9, 1992
Published version (DOI)

Trimethylsilyl bromide (TMSBr) in the presence of catalytic ZnI2 induces facile substitution of allylic acetates to the bromides with or without rearrangement as governed by product stability. This was applied to the preparation of a key intermediate employed in the synthesis of important cannabinoid metabolites. © 1992.

Duke Scholars

Michael Anthony Moody
Author Michael Anthony Moody Pediatrics, Infectious Diseases

Published In

Tetrahedron Letters

DOI

10.1016/S0040-4039(00)92658-3

ISSN

0040-4039

Publication Date

June 9, 1992

Volume

33

Issue

24

Start / End Page

3443 / 3446

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Seltzman, H. H., Moody, M. A., & Begum, M. K. (1992). Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide. Tetrahedron Letters, 33(24), 3443–3446. https://doi.org/10.1016/S0040-4039(00)92658-3
Seltzman, H. H., M. A. Moody, and M. K. Begum. “Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide.” Tetrahedron Letters 33, no. 24 (June 9, 1992): 3443–46. https://doi.org/10.1016/S0040-4039(00)92658-3.
Seltzman HH, Moody MA, Begum MK. Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide. Tetrahedron Letters. 1992 Jun 9;33(24):3443–6.
Seltzman, H. H., et al. “Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide.” Tetrahedron Letters, vol. 33, no. 24, June 1992, pp. 3443–46. Scopus, doi:10.1016/S0040-4039(00)92658-3.
Seltzman HH, Moody MA, Begum MK. Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide. Tetrahedron Letters. 1992 Jun 9;33(24):3443–3446.
Journal cover image

Published In

Tetrahedron Letters

DOI

10.1016/S0040-4039(00)92658-3

ISSN

0040-4039

Publication Date

June 9, 1992

Volume

33

Issue

24

Start / End Page

3443 / 3446

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry