Reaction of Carbodiimides with trifluoromethanesulfonic acid |
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| Authors: | L L Tolstikova B A Shainyan N N Chipanina |
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| Institution: | 1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia
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| Abstract: | Carbodiimides RN=C=NR (R = i-Pr, c-C6H11, Ph) react with trifluoromethanesulfonic acid with successive formation of O-triflyl isoureas RNHC(OTf)=NR, the isomeric N-triflyl ureas RN(Tf)C(O)NHR, and symmetrically substituted ureas RNHC(O)NHR. Carbodiimide Me3SiN=C=NSiMe3 in the reaction with TfOH undergoes desilylation to afford ester CF3SO2OSiMe3 and unsubstituted carbodiimide (cyanamide), which gives the products of di- and trimerization and urea. |
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