The Journal of Organic Chemistry

Synthesis of 3, 8-dihydroxyspiro [4.4] nona-3, 8-diene-27-dione via a diacyloin condensation

C Ainsworth, F Chen

Index: Ainsworth,C.; Chen,F. Journal of Organic Chemistry, 1970 , vol. 35, # 5 p. 1272 - 1274

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Citation Number: 3

Abstract

Tetramethyl methanetetraacetate and sodium formed an intermediate dienediol that was oxidized by air or iodine to give the title compound. The intermediate in the oxidation with iodine appears to be a disemidione. A modified acyloin condensation, using sodium-liquid ammonia followed by evaporation of the ammonia and the addition of trimethylchlorosilane (TMCS), has been shown to be of particular utility in the synthesis of