Issue 20, 1990

Cycloadditions of alkynyl esters and ethers with 1,2,3-tri-t-butyl azete

Abstract

Moderately electron-rich alkynes, such as alkynyl carboxylates 2a, b, siloxyalkynes 2c, d, an alkynyl p-toluenesulphonate 2e, and ethoxyacetylene 2f, add exclusively to the C[double bond, length half m-dash]N bond of the kinetically stabilized azete 1; with terminal alkynes 2a, f, a mixture of the regioisomeric 1-Dewar-pyridines 3 and 4 is obtained, whereas addition of internal alkynes results only in 3-oxy-1-Dewar-pyridines 3.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1990, 1456-1457

Cycloadditions of alkynyl esters and ethers with 1,2,3-tri-t-butyl azete

G. Mass, M. Regitz, R. Rahm, J. Schneider, P. J. Stang and C. M. Crittell, J. Chem. Soc., Chem. Commun., 1990, 1456 DOI: 10.1039/C39900001456

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