ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

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.

[img] PDF
fulltext.pdf
Restricted to Registered users only

Download (757Kb) | Request a copy

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
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.ernet.in/id/eprint/14627

Actions (login required)

View Item View Item