The Journal of Organic Chemistry

Remote dianions. IV. 4-(Phenylsulfonyl) butanoic acid. Preparation, dianion generation, and application to four-carbon chain extension

CM Thompson, JA Frick

Index: Thompson, Charles M.; Frick, Jeffrey A. Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 890 - 896

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Citation Number: 14

Abstract

The bishomoenolate dianion of 4-(phenylsulfonyl) butanoic acid was investigated. It was observed that the dianion could be generated in greater than 95% yield with 200 mol% of n- BuLi at certain concentrations. The dianion was reacted with a variety of aldehydes to afford, after cyclization, substituted tetrahydropyran-2-ones (lactones). These derivatives were reductively eliminated to afford methyl 4-butenoates in yields of 56-8570.

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