Rao, Subha GSR and Bhaskar, Vijaya K (1993) Synthesis based on cyclohexadienes. Part 8. Synthesis of 1-methylbicyclo[2.2.2]oct-2-enecarboxylate derivatives. In: Journal of the Chemical Society, Perkin Transactions 1 (19). pp. 2333-2337.
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The 1,4-dihydrotoluic acids, obtained by the Birch reduction of 2-methyl- and 3-methyl-benzoic acids are isomerised to 2-methylcyclohexa-1,5-diene-1-carboxylic acid 10 and 5-methylcyclohexa-1,5-diene-1-carboxylic acid 15, respectively. These conjugated diene acids undergo facile cycloaddition with dienophiles resulting in bicyclo[2.2.2]octene derivatives having a bridgehead methyl group. While the cycloaddition of 10 with dienophiles produces regioisomeric mixture of adducts, the acid 15 affords regiospecific products.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Royal Society of Chemistry.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||01 Jul 2008|
|Last Modified:||19 Sep 2010 04:46|
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