Abstract
New acceptor-substituted allenyl halides were synthesized. The addition of hydrazoic acid (HN 3 ) to these allenyl halides led to the formation of new 1-azido-2-haloethene derivatives. The photolysis of the latter compounds afforded the corresponding 2-halo-2H-azirines. At room temperature or below, they isomerized irreversibly by [ 1,2]-rearrangement of halogen to form other azirine isomers in very good yields. It is the first time that such a complete rearrangement of 2-halo-2H-azirines is observed. This synthetic strategy offers the possibility to observe both azirine isomers in their pure forms from single 1-azido-2-haloethene precursor.
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