ACETYLENES WITH ELECTRON DONOR AND ACCEPTOR GROUPS

Acetylenes having both electrondonating and electronaccepting groups (1) may be obtained in good yield from the correspondingly substituted olefines via bromination and elimination of HBr. The reaction of the acetylene aldehyde 1a with proton acids yields, after rearrangement of the primary adducts, the β‐substituted acrylamides. Addition of nucleophiles leads to the β‐disubstituted α.β‐unsaturated carbonyl compounds. With hydrazines one obtains pyrazoles and pyrazolones. The acetylenes 1 undergo [2+2]‐, [2+3]‐ and [2+4]‐cycloaddition reactions. Copyright © 1969 Verlag GmbH & Co. KGaA, Weinheim