Aliphatic semidiones. XV. 2, 3-Semidiones derived from the bicyclo [n. 1.0] alkanes

GA Russell, JJ McDonnell, PR Whittle…

Index: Russell,G.A. et al. Journal of the American Chemical Society, 1971 , vol. 93, # 6 p. 1452 - 1466

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Citation Number: 26

Abstract

Abstract: The synthesis of bicyclo [2.1. O] pentane-, bicyclo [3.1. O] hexane-, bicyclo [4.1. O] heptane-, bicyclo [5.1. O] octane-, and bicyclo [6.1. O] nonane-2, 3-semidiones has been investigated. Acyloin condensations of cis-l, 2-cyclopropanedicarboxylic esters failed to yield bicyclopentane semidiones. Instead, the ring-opened cyclopentanesemidiones were formed. Acyloin condensation or oxidation of the 2-or 3-ketones in basic solution ...