14528-67-7Relevant articles and documents
FACILE SYNTHESIS OF AZIDES: CONVERSION OF HYDRAZINES USING DINITROGEN TETROXIDE
Kim, Yong Hae,Kim, Kweon,Shim, Sung Bo
, p. 4749 - 4752 (1986)
Various hydrazines such as aryl-, carbonyl-, and sulfonylhydrazine were reacted with dinitrogen tetroxide to give the corresponding azides in excellent yields under mild conditions at low temperature (-20 to ca.-40 deg C) in acetonitrile.
Visible Light-Induced Regioselective Cycloaddition of Benzoyl Azides and Alkenes to Yield Oxazolines
Bellotti, Peter,Brocus, Julien,El Orf, Fatima,Selkti, Mohamed,K?nig, Burkhard,Belmont, Philippe,Brachet, Etienne
supporting information, p. 6278 - 6285 (2019/05/24)
Visible light catalysis allows the regioselective synthesis of oxazolines in high yields. The mild photosensitized manifold leverages the intermolecular formation of oxazolines with a wide functional group tolerance on both benzoyl azides and alkenes part
Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles
Kumar, Ravi,Arigela, Rajesh K.,Kundu, Bijoy
, p. 11807 - 11812 (2015/08/11)
An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).