Hydrocarbons, hydrocarbon groups s. a. Hydrogenolysis

Hydrocarbons, hydrocarbon groups (s. a. Hydrogenolysis, Replacement of hydrogen)... 

Hydrocarbons, hydrocarbon groups (s. a. Hydrogenolysis, Replacement by hydrogen) —, alkylation 12, 851 13, 805 —, carbanion reactions 13, 839... 

Hydrogenolysis can occur using dissolving metal conditions, and is particularly useful for the cleavage of O-benzyl and N-benzyl derivatives. It is widely used as a useful alternative to catalytic hydrogenation. Treatment with sodium in ammonia cleaves the O-benzyl group, as in the conversion of 491 to 492 (in 90% yield), in Mulzer s synthesis of hastanecine. l Note that the byproduct is toluene. It is also possible to cleave other reactive C—O (or C—N) bonds. Allylic acetates, for example, are cleaved to the hydrocarbon, as shown by the reaction of 493 with lithium and ammonia to give an 81% yield of 494. ... 

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