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The Reaction of Patchoulol with Lead Tetraacetate, a Regiospecific Fragmentation

✍ Scribed by Alan F. Thomas; Michel Ozainne

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
519 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Patchoulol (1) forms 2,2,6,8‐tetramethylbicyclo [5.3.1]undec‐7‐en‐3‐one (5) with lead tetraacetate. This ketone undergoes acid‐catalyzed cyclization to 2,6,6,10‐tetramethyltricyclo [5.3.1.0^1,5^]undec‐9‐en‐5‐ol (10), and is reduced to 2 stereoisomeric alcohols with lithium aluminium hydride. One of these alcohols 8 is readily dehydrated with cyclization to 2,6,6,10‐tetramethyltricyclo [5.3.1.0^1,5^]undec‐9‐ene (12) and a double bond isomer 13, longer treatment with acid resulting in a Wagner‐Meerwein rearrangement to a mixture of two 1,3,7,7‐tetramethyltricyclo [6.2.1.0^2,6^]‐undecenes (19 and 20), isomeric with β‐patchoulene (23). The other alcohol 7 with p‐toluenesulfonic acid forms the cyclic ether, 1,3,7,7‐tetramethyl‐11‐oxatricyclo‐[4.4.1.1^2,8^]dodecane (15).

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## Abstract The reaction of norbornene with lead tetraacetate is found to be much more complex than previously reported. In acetic acid and in benzene, the __syn__‐7‐norbornenyl, 3‐nortricyclyl, and __syn__ and __anti__‐7‐acetoxy‐__exo__‐2‐norbornyl acetates were characterized. In methanol, the iso