Hydrogenation of 2, 5-diacetoxy-2, 5-dimethyl-3-hexyne over palladium

DR Paulson, LS Gilliam, VO Terry, SM Farr…

Index: Paulson,D.R. et al. Journal of Organic Chemistry, 1978 , vol. 43, # 9 p. 1783 - 1787

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Citation Number: 5

Abstract

The hydrogenation of 1 over 10% palladium on charcoal proceeds to give seven products (2- 8). Alkene 2 is the precursor of the other products. A concerted process including hydrogenation, hydrogenolysis, and isomerization is postulated to account for the direct formation of 5 from 2. The effect of added nitrogen bases on the product distribution ic; presented, and several mechanistic alternatives are discussed.