Base‐Catalyzed Conversion of an Equatorial into an Axial Methoxycarbonyl Group Due to a 1,5‐Long‐Range Substituent Effect

Raphael Mechoulam, Naftali Lander, Ilana Tamir, Zvi Ben‐Zvi, Yosef Kimmel

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The unusual transformation of an equatorial CO2Me group into an axial one has been observed in the hexahydrocannabinol skeleton [2a → 1a, R = Ac]. In the methyl ethers, however, the expected reaction takes place [1b → 2b, R = Me]. The epimerization of 2a in the presence of strong bases is attributed to the potential phenolate ion situated five carbon atoms away. (Figure Presented.)

Original languageEnglish
Pages (from-to)543
Number of pages1
JournalAngewandte Chemie - International Edition
Volume19
Issue number7
DOIs
StatePublished - 1 Jan 1980
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

Fingerprint

Dive into the research topics of 'Base‐Catalyzed Conversion of an Equatorial into an Axial Methoxycarbonyl Group Due to a 1,5‐Long‐Range Substituent Effect'. Together they form a unique fingerprint.

Cite this