Reactions of unsaturated azides; Part 17: An efficient strategy for the synthesis of small-ring heterocycles via isomerization of 2-halo-2H-azirines

Content Provider	Semantic Scholar
Author	Fotsing, Joseph R. Banert, Klaus
Copyright Year	2006
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.
Starting Page	261
Ending Page	272
Page Count	12
File Format	PDF HTM / HTML
DOI	10.1055/s-2005-918513
Alternate Webpage(s)	http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-2005-918513.pdf
Alternate Webpage(s)	https://doi.org/10.1055/s-2005-918513
Volume Number	2006
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article