reaction of propanoic acid with lead iv acetate
Answers
Answer:
Tetrahedron Letters No.36, pp, 4363-4367, 1966. Pcrgamn Press Ltd.
Printed in Great Britain.
LEAD (IV) ACETATE OXIDATION OF UNSATURATED CARBOXYLIC ACIDS, ESTERS
AND AMIDES. THE MECHANISM OF THE REACTION
Robert M. Moriarty, Harold G. Walsh and Harsh Gopal
Department of Chemistry
The Catholic University of America
Washington, D.C. 20017
(Received 25 June 1966)
Lead tetraacetate oxidation of saturated carboxylic acids causes decarboxylatioq
with formation of the corresponding lower acetate and alkene’ . Koch1 *2 has presented
excellent evidence in support of a free rodica’ chain mechanism for the oxidative decarboxylation.
In the case of certain unsaturated carboxylic acids the oxidation takes a markedly
different course. Instead of oxidative decarboxylation, intramolecular acetoxy lactone
formation occurr3. We wish to report on the synthetic utility of this reaction as well as
the mechanistic pathway by which it proceeds. Typically endo+carboxy-bicycle
[2,2,j]hept-2-ene (J, upon lead tetraacetate oxidation in either benzene or pyridine,
was found to yield acetoxy lactone I@’ in 80% yield. Similar oxidation of
A2-cyc’opentenyl acetic acid (IJI) yielded acetoxy lactone (m5 in 70% yield. Only
in the oxidation of endo-5-corboxybicyclo[2,2,2]oct-2-ene 0 was substantial
decarboxylation observed, and about 15% of the known M-acetoxy-6a-hydroxybicyclo
[2,2,2j’octane 2a-carboxy’ic 6a-lactone (Vl)4b was obtained6
Explanation: