The alkaline cleavage of N-nitroso-N-prop-2-ynylamides (1) and (9) in methanol and the photolysis of alkynone tosylhydrazones (4) and (10) in methanol–sodium methoxide afforded both allenyl and prop-2-ynyl methyl ethers; the site of protonation of diazopropynes and the reactivity of prop-2-ynyldiazonium ions have been investigated.
W. Kirmse and J. Heese, J. Chem. Soc. D, 1971, 258 DOI: 10.1039/C29710000258
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