Bond fixation in annulenes. 16. Synthesis of the 1, 2-dimethyl-3-phenylcyclooctatetraene. dblarw. 1, 8-dimethyl-2-phenylcyclooctatetraene bond shift isomer pair. …

…, KJ McCullough, R Samodral, G DeLucca…

Index: Paquette, Leo A.; Gardlik, John M.; McCullough, Kevin J.; Samodral, Rodney; DeLucca, George; Ouellette, Robert J. Journal of the American Chemical Society, 1983 , vol. 105, # 26 p. 7649 - 7655

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Citation Number: 11

Abstract

Abstract: Two synthetic approaches to the cyclooctatetraene bond shift isomers 3 F? 4 were developed. The first began with a phenyl-substituted starting material (phenylsuccinic acid) and proceeded to introduce the two methyl groups by desulfonylative ring contraction of a bicyclic a, cY'-disubstituted sulfone. The second had its origins in citraconic anhydride. The two carbonyl groups were differentiated by regiospecific conversion to bromo lactone 20. ...