Subba Rao, G. S. R. ; Vijaya Bhaskar, K. (1993) Synthesis based on cyclohexadienes. Part 8. Synthesis of 1-methylbicyclo[2.2.2]oct-2-enecarboxylate derivatives Journal of the Chemical Society, Perkin Transactions 1 (19). pp. 2333-2337. ISSN 1472-7781
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Official URL: http://pubs.rsc.org/en/content/articlelanding/1993...
Related URL: http://dx.doi.org/10.1039/P19930002333
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: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 55735 |
| Deposited On: | 19 Aug 2011 03:28 |
| Last Modified: | 19 Aug 2011 03:28 |
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