Synthesis based on cyclohexadienes. Part 8. Synthesis of 1-methylbicyclo[2.2.2]oct-2-enecarboxylate derivatives

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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Abstract

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
Publication:	Journal of the Chemical Society, Perkin Transactions 1
Publisher:	Royal Society of Chemistry
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
URI:	http://eprints.iisc.ac.in/id/eprint/14627

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