13C magnetic resonance studies. 142. The fate of highly substituted acyclic ketones in strong base: β-enolization, Haller-Bauer cleavage, and an alkyl to aryl acyl shift

RA Dyllick-Brenzinger, V Patel…

Index: Dyllick-Brenzinger, Rainer A.; Patel, Vijay; Rampersad, Mollin B.; Stothers, J. B.; Thomas, Shirley E. Canadian Journal of Chemistry, 1990 , vol. 68, # 7 p. 1106 - 1115

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Citation Number: 5

Abstract

Di-tert-butyl ketone (2 a), 5, 5, 7, 7-tetramethyl-6-undecanone (2 b), and 2, 4-dimethyl-2, 4- diphenyl-3-pentanone (2 d) have been found to undergo slow rearrangement by β-proton abstraction from the α-methyl groups upon treatment with t-BuO-/t-BuOH/≥ 185° C. This is in contrast to the absence of such rearrangement in cyclic systems. It is the only significant process observed for 2 a and 2 b, whereas with 2 d and its monomethyl analog 22 Haller- ...