The ring opening of pyridazine 1 -oxide by the Grignard reagents prepared from 3-bromochlorobenzene, bromobenzene, 1 -bromonaphthalene, pent-1 -yne, and 1 -phenylbut-1 -en-3-yne is shown to lead exclusively to the corresponding terminal E-enynes (3a), (3b), (5), (6), and (7) respectively. By contrast, alkyl Grignard reagents instead lead to the corresponding 1, 3-dienes (9).
L. Crombie, N. A. Kerton and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1979, 2136 DOI: 10.1039/P19790002136
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