N-phosphonio formamidine derivatives: Synthesis,characterization, X-ray crystal structures,and deprotonation reactions |
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| Authors: | Thanh Dung Le Damien Arquier Laure Vendier Stéphanie Bastin Thi Kieu Xuan Huynh Alain Igau |
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| Affiliation: | 1. CNRS, laboratoire de chimie de coordination (LCC), 205, route de Narbonne, 31077 Toulouse, France;2. UPS, INPT, LCC, université de Toulouse, 31077 Toulouse, France;3. Department of Analytical Chemistry, School of Chemistry, University of Science, Vietnam National University 227, Nguyen Van Cu, District 5, Ho Chi Minh City, Vietnam;4. Department of Inorganic and Applied Chemistry, School of Chemistry, University of Science, Vietnam National University, 227, Nguyen Van Cu, District 5, Ho Chi Minh City, Vietnam |
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| Abstract: | A simple and efficient method for the preparation of N-phosphonio formamidine derivatives of the general formula [R”2N?C(H)=N?P(R’)R2]+X? is described. The data recorded in solution and the single crystal X-ray studies revealed that these compounds are best described by the combination of the two mesomeric N-phosphonio formamidine [R”2N?C(H)=N?P(R’)R2]+ and iminium phosphazene [R”2N=C(H)?N=P(R’)R2]+ forms. Formamidine phosphorus ylides iPr2N?C(H)=N?P(CH2)R2 were prepared after addition of tBuLi at –78 °C from the corresponding N-phosphonio compounds. [(PhCN)2Pd(Cl)2] was reacted with iPr2N?C(H)=N?P(CH2)iPr2 to form the dimeric complex [(iPr2N?C(H)=N?P(CH2)iPr2)Pd(Cl)(μ-Cl)]2 which was structurally characterized by X-ray analysis. The deprotonation reactions conducted on [iPr2N?C(H)=N?PPh3]+X? occurred via an intramolecular rearrangement to give the cyanamide compound iPr2N?C≡N and PPh3; transient formation of the amino-phosphazene-carbene iPr2N?C?N=PPh3 was not observed. |
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