REACTION OF DIPHENOXYPHOSPHORYLCHLORIDE WITH N,N-DISUBSTITUTED UREAS - FORMATION OF PHOSPHORYLATED BIURET COMPOUNDS

被引:2
作者
HERRMANN, E
NGUYEN, TTC
OHMS, G
JONES, PG
机构
[1] TECH UNIV DRESDEN,CHEM ABT,O-8027 DRESDEN,GERMANY
[2] TECH UNIV BRAUNSCHWEIG,INST ANORGAN & ANALYT CHEM,W-3300 BRAUNSCHWEIG,GERMANY
来源
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE | 1991年 / 594卷 / 03期
关键词
DIPHENOXYPHOSPHORYLCHLORIDE; N'; N'-DIALKYL-N-DIPHENOXYPHOSPHORYL UREA; N-DIPHENOXYPHOSPHORYL-N'; N'-DIPROPYL BIURET; X-RAY CRYSTAL STRUCTURE ANALYSIS; NMR SPECTRA;
D O I
10.1002/zaac.19915940118
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
N',N'-disubstituted N-diphenoxyphosphorylureas, (PhO)2P(O)-NH-CO-NR1R2 (R1 = R2 = Et, 1; n-Pr, 2; n-Bu, 3; i-Bu, 4; R1 = Me and R2 = Ph, 5) as well as phosphorylated biuret compounds, (PhO)2P(O)-NH-CO-NH-CO-NR1R2 are obtained in the reaction of diphenoxyphosphorycholride with N,N-disubstituted ureas and triethylamine. The biuret derivatives are formed via (PhO)2P(O)NCO. Theiry ield rises if the reaction is carried out without amine. The X-ray crystal structure analysis of (PhO)2P(O)-NH-CO-NH-CO-NPr2, 8, shows that dimers exist in the crystal with intermolecular as well as intramolecular hydrogen bonds. The framework formed by atoms P-N1-C1(O4)-N2-C2(O5)-N3(C3)C6 is planar. The existence of a rotation barrier along the bond C2-N3 was detected by NMR spectroscopy.
引用
收藏
页码:146 / 156
页数:11
相关论文
共 11 条
[1]   ATOM HYBRIDIZATION AND BOND PROPERTIES - SOME CARBON-CONTAINING BONDS [J].
BROWN, MG .
TRANSACTIONS OF THE FARADAY SOCIETY, 1959, 55 (05) :694-701
[2]  
CORBRIDGE DEC, 1978, PHOSPHOROUS OUTLINE, P26
[3]  
Kessler V. H., 1970, ANGEW CHEM, V82, P237
[4]  
KIRSANOV AV, 1958, ZH OBSHCH KHIM+, V28, P1595
[5]   DYNAMIC NMR-STUDIES OF HINDERED ROTATION ON N-C(X) BOND INCREMENT .16. CENTRAL METAL ATOM INFLUENCE ON ROTATIONAL BARRIERS OF THE RESTRICTED C,N-ROTATION AND THE C-13 NMR-SPECTRA OF THE METAL-COMPLEXES OF 1,1-DIETHYL-3-BENZOYL-THIO(SELENO) UREA [J].
KLEINPETER, E ;
BEHRENDT, S ;
BEYER, L .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1982, 495 (12) :105-114
[6]   ON THE PHOSPHORYLATION OF N,N-DIMETHYLUREA WITH POCL3 - N,N-DIMETHYLBIURETOPHOSPHATE [J].
LEHMANN, HA ;
SCHAFFRATH, W .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1984, 508 (01) :145-148
[7]   PHOSPHORIC-ACID UREIDES [J].
MARKALOU.F ;
BERANEK, J ;
CERNIK, M ;
TOUZIN, J ;
JERMAN, Z .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1972, 37 (03) :725-&
[8]  
SCHAFFRATH W, 1974, Patent No. 190528
[9]  
SCHAFFRATH W, 1975, Patent No. 113551
[10]   DIPHENYLPHOSPHINYL UREAS [J].
UTVARY, K ;
FREUNDLI.E ;
GUTMANN, V .
MONATSHEFTE FUR CHEMIE UND VERWANDTE TEILE ANDERER WISSENSCHAFTEN, 1966, 97 (02) :348-&