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DOI: 10.1055/s-2005-918513
Reactions of Unsaturated Azides; Part 17: [1] An Efficient Strategy for the Synthesis of Small-Ring Heterocycles via Isomerization of 2-Halo-2H-azirines
Publication History
Publication Date:
21 December 2005 (online)
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Abstract
New acceptor-substituted allenyl halides were synthesized. The addition of hydrazoic acid (HN3) 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.
Key words
allenes - azides - 2-halo-2H-azirines - addition reactions - rearrangements - photochemistry - thermolysis
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References
An alleged 2-methylene-2H-azirine [14] proved to be a structurally isomeric product. [15]