Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement

Amiram Goldblum; Raphael Mechoulam

doi:10.1039/P19770001889

Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement

Amiram Goldblum, Raphael Mechoulam^*

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Various enol benzoates were oxidized with sodium chromate in acetic acid and acetic anhydride. Allylic oxidation (leading to 1 -benzoyloxy-3-0xoalk-l -enes) and a novel oxidative rearrangement (leading to a-benzoyloxyketones) in varying yields were the major reactions observed. The implications of these findings are discussed.

Original language	American English
Pages (from-to)	1889-1898
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19770001889
State	Published - 1977

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title = "Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement",

abstract = "Various enol benzoates were oxidized with sodium chromate in acetic acid and acetic anhydride. Allylic oxidation (leading to 1 -benzoyloxy-3-0xoalk-l -enes) and a novel oxidative rearrangement (leading to a-benzoyloxyketones) in varying yields were the major reactions observed. The implications of these findings are discussed.",

author = "Amiram Goldblum and Raphael Mechoulam",

year = "1977",

doi = "10.1039/P19770001889",

language = "American English",

pages = "1889--1898",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Chemical Society",

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T1 - Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement

AU - Goldblum, Amiram

AU - Mechoulam, Raphael

PY - 1977

Y1 - 1977

N2 - Various enol benzoates were oxidized with sodium chromate in acetic acid and acetic anhydride. Allylic oxidation (leading to 1 -benzoyloxy-3-0xoalk-l -enes) and a novel oxidative rearrangement (leading to a-benzoyloxyketones) in varying yields were the major reactions observed. The implications of these findings are discussed.

AB - Various enol benzoates were oxidized with sodium chromate in acetic acid and acetic anhydride. Allylic oxidation (leading to 1 -benzoyloxy-3-0xoalk-l -enes) and a novel oxidative rearrangement (leading to a-benzoyloxyketones) in varying yields were the major reactions observed. The implications of these findings are discussed.

UR - http://www.scopus.com/inward/record.url?scp=84918615518&partnerID=8YFLogxK

U2 - 10.1039/P19770001889

DO - 10.1039/P19770001889

M3 - Article

AN - SCOPUS:84918615518

SN - 1470-4358

SP - 1889

EP - 1898

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement

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