Formation of trianions of 2, 4, 6-triketones. Synthesis of 3, 5, 7-triketo acids using lithium diisopropylamide

TM Harris, GP Murphy, AJ Poje

Index: Harris,T.M. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 7733 - 7741

Full Text: HTML

Citation Number: 24

Abstract

Abstract: Ionization of the methyl group of l-phenyl-1, 3-butanedione (1) and of I-phenyl-I, 3, 5-hexanetrione (2) by KNH?. NaNH?, and LiNH? in liquid NH3 has been studied by measurement of deuterium loss from the methyl-deuterated species. KNH? and NaNH? brought about rapid and complete formation of the dianion of 1; formation of trianion with 2 was slow and failed to go to completion. Reversibility led to loss of> 1. OD/methyl group ...