Organic reactions in strong alkalis. Part VII. Fission of unsaturated acids by alkali fusion in potassium deuterioxide

Abstract

Representative alkenoic, alkynoic and alkadienoic acids have been subjected to alkali fusion with potassium deuteroxide. The deuteriated degradation products have been examined by n.m.r. spectroscopy and mass spectrometry. The deuteriation patterns of the fission products are shown to be consistent with a stepwise reversible migration of the unsaturated function during the fusion reaction.

Under the conditions of alkali fusion (potassium deuteroxide at 360°) hydrogen–deuterium exchange occurs on the benzene nucleus, as shown by the reactions of benzoic and 4-phenylbutanoic acids and of their p-t-butyl derivatives.