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

doi:10.1002/anie.198005431

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 journal › Article › peer-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 language	English
Pages (from-to)	543
Number of pages	1
Journal	Angewandte Chemie - International Edition
Volume	19
Issue number	7
DOIs	https://doi.org/10.1002/anie.198005431
State	Published - 1 Jan 1980
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry

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

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.)",

author = "Raphael Mechoulam and Naftali Lander and Ilana Tamir and Zvi Ben‐Zvi and Yosef Kimmel",

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AU - Mechoulam, Raphael

AU - Lander, Naftali

AU - Tamir, Ilana

AU - Ben‐Zvi, Zvi

AU - Kimmel, Yosef

PY - 1980/1/1

Y1 - 1980/1/1

N2 - 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.)

AB - 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.)

UR - https://www.scopus.com/pages/publications/84985569580

U2 - 10.1002/anie.198005431

DO - 10.1002/anie.198005431

M3 - Article

AN - SCOPUS:84985569580

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VL - 19

SP - 543

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

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

Abstract

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