Issue 19, 1993
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

G. S. R. Subba Rao  and  K. Vijaya Bhaskar  

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.

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Article information

DOI
https://doi.org/10.1039/P19930002333
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 2333-2337

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

G. S. R. S. Rao and K. V. Bhaskar, J. Chem. Soc., Perkin Trans. 1, 1993, 2333 DOI: 10.1039/P19930002333

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