Reactions of Unsaturated Azides; Part 17:An Efficient Strategy for the Synthesis of Small-Ring Heterocycles via Isomerization of 2-Halo-2H-azirines
| العنوان: | Reactions of Unsaturated Azides; Part 17:An Efficient Strategy for the Synthesis of Small-Ring Heterocycles via Isomerization of 2-Halo-2H-azirines |
|---|---|
| المؤلفون: | Joseph R. Fotsing, Klaus Banert |
| المصدر: | Synthesis. :261-272 |
| بيانات النشر: | Georg Thieme Verlag KG, 2006. |
| سنة النشر: | 2006 |
| مصطلحات موضوعية: | Azirine, Addition reaction, Organic Chemistry, Photodissociation, Halide, General Medicine, Photochemistry, Ring (chemistry), Medicinal chemistry, Catalysis, chemistry.chemical_compound, chemistry, Halogen, Hydrazoic acid, Halo, Isomerization |
| الوصف: | 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. |
| تدمد: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-2005-918513 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0d69afa7bca297d5f936936468ef3a88 https://doi.org/10.1055/s-2005-918513 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....0d69afa7bca297d5f936936468ef3a88 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 1437210X 00397881 |
|---|---|
| DOI: | 10.1055/s-2005-918513 |