Preparation of urethane and urea derivatives of (NPCl2)3
| Autor: | Harm Pol, Pieter Lykle Buwalda, Auke Meetsma, A. P. Jekel, Adri A. van der Huizen, Johan C. van de Grampel, Theo Wilting |
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| Jazyk: | angličtina |
| Rok vydání: | 1994 |
| Předmět: | |
| Zdroj: | Journal of the Chemical Society-Dalton Transactions, 577-581. ROYAL SOC CHEMISTRY ISSUE=4;STARTPAGE=577;ENDPAGE=581;ISSN=0300-9246;TITLE=Journal of the Chemical Society-Dalton Transactions |
| ISSN: | 0300-9246 |
| Popis: | Reactions of (NPCl2)3 with NaNCO in the presence of aliphatic alcohols have been investigated. Using an equimolar amount of NaNCO in refluxing acetonitrile, high yields of mono(urethane) derivatives N3P3Cl5(NHCO2R) were obtained. Disubstitution is mainly non-geminal. Reactions of (NPCl2)3 with AgNCO and methanol in acetonitrile follow a quite different pattern and lead to the formation of three products with basically geminal structures, e.g. gem-N3P3Cl4(OR)(NHCO2R), gem-N3P3Cl4(NH-CO2R)2, and a spiro derivative (NPCl2)2NP[N(CO2R)C(O)NHC(CH3)N]. The crystal structure of the last compound (R = CH3) has been determined. The difference between the reaction pathways observed for NaNCO and AgNCO is discussed in terms of S(N)2 and S(N)1 mechanisms, respectively. An improved synthesis of (NPCl2)2NP(NH2)(NCO) and its reactions with alcohols and amines are described. |
| Databáze: | OpenAIRE |
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