Supplementary Material. Novel N-phosphorylated iminophosphoranes based on 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide
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1 Supplementary Material Novel N-phosphorylated iminophosphoranes based on 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide Michael Weinert, a Olaf Fuhr, b and Manfred Döring* c a Fraunhofer Institute for Chemical Technology ICT, Pfinztal, Germany b Institute of Nanotechnology (INT) and Karlsruhe Nano Micro Facility (KNMF), Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen, Germany c Fraunhofer Institute for Structural Durability and System Reliability LBF, Division Plastics, Darmstadt, Germany manfred.doering@lbf.fraunhofer.de Table of Contents P-NMR spectra S C-NMR spectra S9 3. Crystallographic data S16 Page S1 ARKAT USA, Inc
2 1. 31 P-NMR spectra 6-Azidodibenzo[c,e][1,2]oxaphosphinin-6-oxid (DOPO-N 3 ) Page S2
3 Trimethyl (6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)phosphorimidate (DOPO-N=P(OMe) 3 ) Page S3
4 Triphenyl (6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)phosphorimidate (DOPO-N=P(OPh) 3 ) Page S4
5 6-((Triphenyl-λ 5 -phosphanylidene)amino)dibenzo[c,e][1,2]oxaphosphinine 6-oxide (DOPO-N=P(Ph) 3 ) Page S5
6 6,6'-((Ethane-1,2-diylbis(diphenyl-λ 5 -phosphanylylidene))bis(azanylylidene))bis(dibenzo[c,e][1,2]oxaphosphinine 6-oxide) ([DOPO-N=P(Ph) 2 CH 2 ] 2 ) Page S6
7 Diphenyl (6-ethoxy-6H-6λ 5 -dibenzo[c,e][1,2]oxaphosphinin-6-ylidene)phosphoramidate ((PhO) 2 (O)P-N=DOP-OEt) Page S7
8 6-((6-ethoxy-6H-6λ 5 -dibenzo[c,e][1,2]oxaphosphinin-6-ylidene)amino)dibenzo[c,e][1,2]oxaphosphinine 6-oxide (DOPO-N=DOP-OEt) Page S8
9 6-Azidodibenzo[c,e][1,2]oxaphosphinin-6-oxid (DOPO-N 3 ) Page S9
10 Trimethyl (6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)phosphorimidate (DOPO-N=P(OMe) 3 ) Page S10
11 Triphenyl (6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)phosphorimidate (DOPO-N=P(OPh) 3 ) Page S11
12 6-((Triphenyl-λ 5 -phosphanylidene)amino)dibenzo[c,e][1,2]oxaphosphinine 6-oxide (DOPO-N=P(Ph) 3 ) Page S12
13 6,6'-((Ethane-1,2-diylbis(diphenyl-λ 5 -phosphanylylidene))bis(azanylylidene))bis(dibenzo[c,e][1,2]oxaphosphinine 6-oxide) ([DOPO-N=P(Ph) 2 CH 2 ] 2 ) Page S13
14 Diphenyl (6-ethoxy-6H-6λ 5 -dibenzo[c,e][1,2]oxaphosphinin-6-ylidene)phosphoramidate ((PhO) 2 (O)P-N=DOP-OEt) Page S14
15 dibenzo[c,e][1,2]oxaphosphinin-6-ylidene)amino)dibenzo[c,e][1,2]oxaphosphinine 6-oxide (DOPO-N=DOP-OEt) Page S15
16 2. Crystallographic data Table 1. Crystallographic data and structure refinement details of DOPO-N=P(OPh) 3, DOPO-N=P(Ph) 3 and [DOPO-N=P(Ph) 2 CH 2 ] 2 2C 3 H 7 OH. Compound DOPO-N=P(OPh) 3 DOPO-N=P(Ph) 3 [DOPO- N=P(Ph) 2 CH 2 ] 2 2C 3 H 7 OH Empirical formula C 30 H 23 NO 5 P 2 C 30 H 23 NO 2 P 2 C 56 H 56 N 2 O 6 P 4 Formula weight Crystal system monoclinic triclinic orthorhombic Space group P2 1 /n P 1 Pbca a/å (3) (5) (4) b/å (8) (6) (14) c/å (3) (8) (14) α/ (5) 90 β/ (12) (4) 90 γ/ (4) 90 Volume/Å (6) (12) (5) Z ρ calc /g cm μ/mm F(000) Crystal size/mm Θ range for data collection/ Reflections collected Independent reflections 5082 [R int = ] 4459 [R int = ] 4881 [R int = ] Ind. refl. with [I 2σ (I)] Data/restraints/parameters 5082/0/ /0/ /0/310 Goodness-of-fit on F Final R indexes [I 2σ (I)] R 1 = , wr 2 = R 1 = , wr 2 = R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = R 1 = , wr 2 = R 1 = , wr 2 = Largest diff. peak/hole / e Å / / / 0.62 CCDC number Page S16 ARKAT USA, Inc
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