Showing papers on "Patchoulol published in 1979"
TL;DR: Patchoulol (1) forms 2,2,6,8-tetramethylbicyclo [5.3.1] with lead tetraacetate as discussed by the authors.
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 [5.3.1.01,5]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 [5.3.1.01,5]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 [6.2.1.02,6]-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-[4.4.1.12,8]dodecane (15).
9 citations
TL;DR: Patchoulol (1) forms 2,2,6,8-tetramethylbicyclo [5.3.1] with lead tetraacetate as discussed by the authors.
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 [5.3.1.01,5]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 [5.3.1.01,5]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 [6.2.1.02,6]-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-[4.4.1.12,8]dodecane (15).
2 citations