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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 3
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Original Articles

Selective Oxidations with Lead Tetraacetate; A Convenient Preparation of 3-Methoxy-4-iso-Propylbehzylalcohol

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Pages 135-141 | Received 14 Nov 1977, Published online: 05 Dec 2006
 

Abstract

Literature reports several examples of oxidation of alkylaromatics with lead tetraacetate and its applications in synthetic organic chemistry1–3. However, there are no systematic studies dealing with preferential oxidation of methyl groups attached to aromatic rings. Investigations presented here show that lead tetraacetate oxidation of aromatic compounds having low ionization potential can lead to preferential oxidation of methyl groups attached to aromatic rings and this selectivity in oxidation has been employed to effect a convenient synthesis of 3, an intermediate in the synthesis of sempervirol4.

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