ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Wharton rearrangement of 2,3-epoxytricyclo[7.1.1.02,7]undecan-3-one, a sterically hindered system, which should have led to an allyl alcohol with the OH group at a bridgehead, gave instead the allylically rearranged alcohol. The desired hydroxy compound was prepared by the Barton modification of the Wharton rearrangement: borohydride reduction to the epoxy alcohols, reaction with N, N′-thiocarbonylbisimidazole, and treatment with Bu3SnH. The bridgehead alcohol (and other 2-oxygenated tricyclo[7.1.1.02,7]undecanes) readily rearranged under acidic or thermal conditions.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720417
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