1078-70-2Relevant articles and documents
SnCl2-catalyzed synthesis of carbamates from renewable origin alcohols
da Silva, Márcio José,Chaves, Diego Morais
, p. 1169 - 1180 (2018)
Effects of structure and reactivity of renewable origin alcohols in the conversion and selectivity of the SnCl2-catalyzed reactions in the presence and absence of urea were assessed. Convenient simple and suitable method for the synthesis of carbamates from renewable origin alcohols and urea in one-step are provided. We have assessed the activity of SnCl2 catalyst, a commercially affordable Lewis acid, in reactions of urea alcoholysis with different natural origin alcohols (geranyl, neryl, bornyl, cinnamyl, α-terpinyl and benzyl alcohols), aiming to synthesize carbamates, which are biologically active compounds, building blocks in organic synthesis and raw material to synthesize polyurethanes. The low cost of urea, the water tolerant catalyst and phosgene free reaction are positive aspects of this carbamates synthesis process. The different reaction pathways were assessed. A mechanism was proposed based on FT-IR experiments and experimental data.
Microwave-Assisted 1,3-Dioxa-[3,3]-Sigmatropic Rearrangement of Substituted Allylic Carbamates: Application to the Synthesis of Novel 1,3-Oxazine-2,4-dione Derivatives
Bou Zeid, Samar,Eid, Samar,Najjar, Fadia,Macé, Aurélie,Rivilla, Ivan,Cossío, Fernando P.,Dorcet, Vincent,Roisnel, Thierry,Carreaux, Fran?ois
, (2021/11/22)
In a first instance, the effect of the microwave irradiation on the 1,3-Dioxa-[3,3]-sigmatropic rearrangement of aryl allylic carbamates was investigated. Under these new conditions, the reaction acceleration was clearly highlighted compared to convention
1,3-Dioxa-[3,3]-sigmatropic Oxo-Rearrangement of Substituted Allylic Carbamates: Scope and Mechanistic Studies
Agirre, Maddalen,Henrion, Sylvain,Rivilla, Ivan,Miranda, José I.,Cossío, Fernando P.,Carboni, Bertrand,Villalgordo, José M.,Carreaux, Fran?ois
, p. 14861 - 14881 (2019/01/04)
An unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment of aryl- and alkenyl-substituted allylic alcohols with activated isocyanates is reported. The reorganization of bonds is highly dependent on the electron density of the aromatic
