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Aziridination of conjugated nitroalkenes

โœ Scribed by Stefania Fioravanti; Lucio Pellacani; Sara Stabile; Paolo A Tardella; Roberto Ballini


Book ID
104256957
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
103 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The recently proposed amination methodology based on solid bases induced decomposition of arenesulphonyloxycarbamates (ArSO3NHCO2Et) has been applied to ct-nitroalkenes, cc-Nitroaziridines have been obtained in high yields and purity, under mild conditions.


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NsOh'l-ICO2Et in the presence of CaO reacts without solvem with ct-nitmalkenes to give l-(etho~l)-2-nitrcaziridines (62-84%). A possible involvement of an aza-Michael route is ~of.,osed on the basis of rcgio-and ~cal reaction outcome, compared also with the results of thermolys/s of ethyl azidoforma

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Conjugated nitroalkenes are readily reduced by a variety of borane and borohydride reagents. The reactions provide a convenient access to a number of nitrogen and oxygen based functional groups.