Co-reporter:Marc Devillard; Richard Declercq; Emmanuel Nicolas; Andreas W. Ehlers; Jana Backs; Nathalie Saffon-Merceron; Ghenwa Bouhadir; J. Chris Slootweg; Werner Uhl;Didier Bourissou
Journal of the American Chemical Society 2016 Volume 138(Issue 14) pp:4917-4926
Publication Date(Web):March 15, 2016
DOI:10.1021/jacs.6b01320
Reaction of the geminal PAl ligand [Mes2PC(═CHPh)AltBu2] (1) with [Pt(PPh3)2(ethylene)] affords the T-shape Pt complex [(1)Pt(PPh3)] (2). X-ray diffraction analysis and DFT calculations reveal the presence of a significant Pt→Al interaction in 2, despite the strain associated with the four-membered cyclic structure. The Pt···Al distance is short [2.561(1) Å], the Al center is in a pyramidal environment [Σ(C–Al–C) = 346.6°], and the PCAl framework is strongly bent (98.3°). Release of the ring strain and formation of X→Al interactions (X = O, S, H) impart rich reactivity. Complex 2 reacts with CO2 to give the T-shape adduct 3 stabilized by an O→Al interaction, which is a rare example of a CO2 adduct of a group 10 metal and actually the first with η1-CO2 coordination. Reaction of 2 with CS2 affords the crystalline complex 4, in which the PPtP framework is bent, the CS2 molecule is η2-coordinated to Pt, and one S atom interacts with Al. The Pt complex 2 also smoothly reacts with H2 and benzamide PhCONH2 via oxidative addition of H–H and H–N bonds, respectively. The ensuing complexes 5 and 7 are stabilized by Pt–H→Al and Pt–NH–C(Ph) = O→Al bridging interactions, resulting in 5- and 7-membered metallacycles, respectively. DFT calculations have been performed in parallel with the experimental work. In particular, the mechanism of reaction of 2 with H2 has been thoroughly analyzed, and the role of the Lewis acid moiety has been delineated. These results generalize the concept of constrained geometry TM→LA interactions and demonstrate the ability of Al-based ambiphilic ligands to participate in TM/LA cooperative reactivity. They extend the scope of small molecule substrates prone to such cooperative activation and contribute to improve our knowledge of the underlying factors.
Co-reporter:Cornelis G. J. Tazelaar, Emmanuel Nicolas, Tom van Dijk, Daniël L. J. Broere, Mitchel Cardol, Martin Lutz, Dietrich Gudat, J. Chris Slootweg and Koop Lammertsma
Dalton Transactions 2016 vol. 45(Issue 5) pp:2237-2249
Publication Date(Web):09 Nov 2015
DOI:10.1039/C5DT03994K
The parent tris(pyrazolyl)phosphine and its 3,5-Me2, 3-Ph, and 3-t-Bu derivatives have been prepared by a simple procedure and show modest Lewis basicity of the phosphorus apex as was established by the magnitude of the 1JP,Se coupling constant of the phosphine selenides. Because of the chelating properties of both the N- and P-sites, neutral phosphorus-centered scorpion ligands allow coordination modes that are unavailable to the abundantly used anionic tris(pyrazolyl)borate scorpionates as we established for Cu(I)-complexation. The substituted P-scorpion ligands only allow for N-coordination, as the P-apex is presumably less accessible. Two X-ray crystal structures were obtained for the Cu-complex of tris(3,5-dimethylpyrazolyl)-phosphine with acetonitrile and triphenylphosphine in the fourth coordination site. The parent P-scorpion ligand can chelate with both its pyrazolyl groups and its P-apex with the product depending on the ratio in which it is mixed with the Cu(I) complex. Reacting two equivalents of the ligand with [Cu(MeCN)4][PF6] resulted in a complex in which Cu is coordinated to the three pyrazolyl groups of one ligand and to the P-apex of the other ligand as confirmed by an X-ray crystal structure determination and a DFT computational analysis. Reacting the ligand and the Cu(I) complex in an equimolar ratio resulted in a remarkable one-dimensional P-scorpion coordination polymer for which a single crystal X-ray structure could be determined. A detailed analysis of the structural features is presented.
Co-reporter:Jan B. M. Wit, G. Bas de Jong, Marius Schakel, Martin Lutz, Andreas W. Ehlers, J. Chris Slootweg, and Koop Lammertsma
Organometallics 2016 Volume 35(Issue 8) pp:1170-1176
Publication Date(Web):April 6, 2016
DOI:10.1021/acs.organomet.6b00227
The phosphinidene complex iPr2N–P═Fe(CO)4 was prepared as a storable phosphirane solution from Collman’s reagent and iPr2NPCl2 in the olefins 1-pentene and 1-hexene. The carbene-like reagent is able to hop under very mild conditions (>−25 °C) from one olefin to another and to alkynes to give the more stable phosphirenes that likewise display dynamic covalent behavior. The olefinic solutions are effective reservoirs for the highly reactive phosphinidene complex, as is illustrated in its N–H and O–H insertion reactions with amines, alcohols, and carboxylic acids and in its P–C bond formation with Grignard reagents.
Co-reporter:Tom van Dijk, Mark K. Rong, Jaap E. Borger, Martin Nieger, J. Chris Slootweg, and Koop Lammertsma
Organometallics 2016 Volume 35(Issue 5) pp:827-835
Publication Date(Web):February 29, 2016
DOI:10.1021/acs.organomet.6b00063
Bis(imino)phosphanes can be synthesized efficiently from iminophosphanes and nitrilium triflates, allowing for nonsymmetric substitution at the imine groups. Symmetrically substituted derivatives can even be obtained in a one-pot procedure from primary phosphanes. These potential N,N-bidentate ligands are sensitive toward Cu(II), Zn(II), and rhodium(I) sources, resulting in loss of an imine group. For [RhCl(COD)]2 this led to an N,P- and P-chelating bimetallic complex. Bis(imino)phosphanes with C-Me substituents rearrange in situ to unique 1,3,5-phosphadiazapentadienes for which a P-coordinated gold(I) complex is reported. The bis(imino)phosphanes are readily oxidized to stable bis(imino)phosphane oxides with aqueous H2O2.
Co-reporter:Tom van Dijk, Martijn S. Bakker, Flip Holtrop, Martin Nieger, J. Chris Slootweg, and Koop Lammertsma
Organic Letters 2015 Volume 17(Issue 6) pp:1461-1464
Publication Date(Web):March 2, 2015
DOI:10.1021/acs.orglett.5b00339
A simple and efficient methodology is presented for the synthesis of a wide range of substituted imines. It is based on stabilizing readily available, but thermally labile, N-alkylnitrilium triflates with pyridine or DMAP to moderately air-stable adducts. These base-stabilized imine synthons react conveniently with phosphorus- and nitrogen-based nucleophiles to amidines and phosphaamidines.
Co-reporter:Tom vanDijk;Dr. Sebastian Burck;Amos J. Rosenthal;Dr. Martin Nieger;Dr. Andreas W. Ehlers;Dr. J. Chris Slootweg;Dr. Koop Lammertsma
Chemistry - A European Journal 2015 Volume 21( Issue 26) pp:9328-9331
Publication Date(Web):
DOI:10.1002/chem.201501126
Abstract
Iminophosphanes are a new group of 1,3-P,N-ligands, readily obtainable from secondary phosphanes and nitrilium ions, having a tunable N-donor site by means of varying the imine substituents. These ligands give, in high yields, monodentate gold complexes and bidentate rhodium and iridium complexes. Crystal structures are reported for both the ligands and the complexes.
Co-reporter:Marc Devillard ;Dr. Emmanuel Nicolas;Dr. Andreas W. Ehlers;Jana Backs;Sonia Mallet-Ladeira;Dr. Ghenwa Bouhadir ;Dr. J. Chris Slootweg;Dr. Werner Uhl;Dr. Didier Bourissou
Chemistry - A European Journal 2015 Volume 21( Issue 1) pp:
Publication Date(Web):
DOI:10.1002/chem.201580161
Co-reporter:Marc Devillard ;Dr. Emmanuel Nicolas;Dr. Andreas W. Ehlers;Jana Backs;Sonia Mallet-Ladeira;Dr. Ghenwa Bouhadir ;Dr. J. Chris Slootweg;Dr. Werner Uhl;Dr. Didier Bourissou
Chemistry - A European Journal 2015 Volume 21( Issue 1) pp:74-79
Publication Date(Web):
DOI:10.1002/chem.201405610
Abstract
Hitherto unknown AuAl interactions have been evidenced upon coordination of the geminal phosphorus–aluminum Lewis pair Mes2PC(CHPh)AltBu2 (Mes=2,4,6-trimethylphenyl). Four different gold(I) complexes featuring alkyl (Me), aryl (Ph, C6F5), and alkynyl (CCPh) co-ligands have been prepared. X-ray diffraction analyses show that PAuAl bridging coordination induces noticeable bending of the ligand (the PCAl bond angle shrinks by 13°). This new type of transition metalLewis acid interaction has been analyzed by DFT calculations.
Co-reporter:Marc Devillard, Emmanuel Nicolas, Christian Appelt, Jana Backs, Sonia Mallet-Ladeira, Ghenwa Bouhadir, J. Chris Slootweg, Werner Uhl and Didier Bourissou
Chemical Communications 2014 vol. 50(Issue 94) pp:14805-14808
Publication Date(Web):06 Oct 2014
DOI:10.1039/C4CC06992G
Coordination of Mes2PC(CHPh)AltBu2 to metal chlorides has been studied. Bridging P→M–Cl→Al coordinations were observed with Rh and Pd fragments, while chloride abstraction systematically occurred with gold. The resulting zwitterionic complexes have been fully characterized and analyzed by DFT calculations.
Co-reporter:Tom vanDijk;Dr. Sebastian Burck;Mark K. Rong;Amos J. Rosenthal;Dr. Martin Nieger;Dr. J. Chris Slootweg;Dr. Koop Lammertsma
Angewandte Chemie 2014 Volume 126( Issue 34) pp:9214-9217
Publication Date(Web):
DOI:10.1002/ange.201405027
Abstract
Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of a novel class of 1,3-P,N ligands as demonstrated for the reaction with primary phosphanes. This procedure allows variation of all substituents. X-ray crystal structures are reported for nitrilium ions, phosphaamidines, and three phosphaamidinate complexes. The lithium phosphaamidinate is N coordinated and its reaction with [AuCl(tht)] (tht=tetrahydrothiophene) gives a unique P-bridged gold trimer, while a P,N-bidentate complex results from [{RhCl(cod)}2]. The nitrilium ion methodology allows extension of the 1,3-P,N motive to bis(imino)phosphanes, which are the neutral phosphorus analogues of the valuable β-diketiminate ligand.
Co-reporter:Andrei Chirila, Robert Wolf, J. Chris Slootweg, Koop Lammertsma
Coordination Chemistry Reviews 2014 s 270–271() pp: 57-74
Publication Date(Web):
DOI:10.1016/j.ccr.2013.10.005
Co-reporter:Tom vanDijk;Dr. Sebastian Burck;Mark K. Rong;Amos J. Rosenthal;Dr. Martin Nieger;Dr. J. Chris Slootweg;Dr. Koop Lammertsma
Angewandte Chemie International Edition 2014 Volume 53( Issue 34) pp:9068-9071
Publication Date(Web):
DOI:10.1002/anie.201405027
Abstract
Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of a novel class of 1,3-P,N ligands as demonstrated for the reaction with primary phosphanes. This procedure allows variation of all substituents. X-ray crystal structures are reported for nitrilium ions, phosphaamidines, and three phosphaamidinate complexes. The lithium phosphaamidinate is N coordinated and its reaction with [AuCl(tht)] (tht=tetrahydrothiophene) gives a unique P-bridged gold trimer, while a P,N-bidentate complex results from [{RhCl(cod)}2]. The nitrilium ion methodology allows extension of the 1,3-P,N motive to bis(imino)phosphanes, which are the neutral phosphorus analogues of the valuable β-diketiminate ligand.
Co-reporter:Dr. Christian Appelt;Dr. J. Chris Slootweg;Dr. Koop Lammertsma;Dr. Werner Uhl
Angewandte Chemie 2013 Volume 125( Issue 15) pp:4350-4353
Publication Date(Web):
DOI:10.1002/ange.201208746
Co-reporter:Dr. Christian Appelt;Dr. J. Chris Slootweg;Dr. Koop Lammertsma;Dr. Werner Uhl
Angewandte Chemie International Edition 2013 Volume 52( Issue 15) pp:4256-4259
Publication Date(Web):
DOI:10.1002/anie.201208746
Co-reporter:Christian Appelt;Dr. J. Chris Slootweg;Dr. Koop Lammertsma;Dr. Werner Uhl
Angewandte Chemie 2012 Volume 124( Issue 24) pp:6013-6016
Publication Date(Web):
DOI:10.1002/ange.201201855
Co-reporter:Cornelis G. J. Tazelaar, Volodymyr Lyaskovskyy, Tom van Dijk, Daniël L. J. Broere, Ludo A. Kolfschoten, Rima Osman Hassan Khiar, Martin Lutz, J. Chris Slootweg, and Koop Lammertsma
Organometallics 2012 Volume 31(Issue 8) pp:3308-3315
Publication Date(Web):March 23, 2012
DOI:10.1021/om300051f
A set of substituted tris(pyrazolyl)phosphine oxides (OP(pzx)3) has been prepared in high yield and applied as neutral scorpion-type ligands. The P apex provides a convenient spectroscopic handle. Substitution at the 3-position of the pyrazolyl ring influences the steric demands of the ligand, while substitution at the 5-position enhances the stability. Copper(I) acetonitrile complexes of the OP(pzx)3 ligands were prepared and tested in ligand exchange reactions with PPh3 and CO. The ν(CO) values of the carbonyl complexes demonstrate the electron-withdrawing properties of the ligands. These observations show that OP(pzx)3 ligands are an interesting extension of the widely used scorpion-type ligands.
Co-reporter:Christian Appelt;Dr. J. Chris Slootweg;Dr. Koop Lammertsma;Dr. Werner Uhl
Angewandte Chemie International Edition 2012 Volume 51( Issue 24) pp:5911-5914
Publication Date(Web):
DOI:10.1002/anie.201201855
Co-reporter:Federica Bertini ; Volodymyr Lyaskovskyy ; Brian J. J. Timmer ; Frans J. J. de Kanter ; Martin Lutz ; Andreas W. Ehlers ; J. Chris Slootweg ;Koop Lammertsma
Journal of the American Chemical Society 2011 Volume 134(Issue 1) pp:201-204
Publication Date(Web):December 13, 2011
DOI:10.1021/ja210214r
Geminal frustrated Lewis pairs (FLPs) are expected to exhibit increased reactivity when the donor and acceptor sites are perfectly aligned. This is shown for reactions of the nonfluorinated FLP tBu2PCH2BPh2 with H2, CO2, and isocyanates and supported computationally.
Co-reporter:Marc Devillard, Emmanuel Nicolas, Christian Appelt, Jana Backs, Sonia Mallet-Ladeira, Ghenwa Bouhadir, J. Chris Slootweg, Werner Uhl and Didier Bourissou
Chemical Communications 2014 - vol. 50(Issue 94) pp:NaN14808-14808
Publication Date(Web):2014/10/06
DOI:10.1039/C4CC06992G
Coordination of Mes2PC(CHPh)AltBu2 to metal chlorides has been studied. Bridging P→M–Cl→Al coordinations were observed with Rh and Pd fragments, while chloride abstraction systematically occurred with gold. The resulting zwitterionic complexes have been fully characterized and analyzed by DFT calculations.
Co-reporter:Cornelis G. J. Tazelaar, Emmanuel Nicolas, Tom van Dijk, Daniël L. J. Broere, Mitchel Cardol, Martin Lutz, Dietrich Gudat, J. Chris Slootweg and Koop Lammertsma
Dalton Transactions 2016 - vol. 45(Issue 5) pp:NaN2249-2249
Publication Date(Web):2015/11/09
DOI:10.1039/C5DT03994K
The parent tris(pyrazolyl)phosphine and its 3,5-Me2, 3-Ph, and 3-t-Bu derivatives have been prepared by a simple procedure and show modest Lewis basicity of the phosphorus apex as was established by the magnitude of the 1JP,Se coupling constant of the phosphine selenides. Because of the chelating properties of both the N- and P-sites, neutral phosphorus-centered scorpion ligands allow coordination modes that are unavailable to the abundantly used anionic tris(pyrazolyl)borate scorpionates as we established for Cu(I)-complexation. The substituted P-scorpion ligands only allow for N-coordination, as the P-apex is presumably less accessible. Two X-ray crystal structures were obtained for the Cu-complex of tris(3,5-dimethylpyrazolyl)-phosphine with acetonitrile and triphenylphosphine in the fourth coordination site. The parent P-scorpion ligand can chelate with both its pyrazolyl groups and its P-apex with the product depending on the ratio in which it is mixed with the Cu(I) complex. Reacting two equivalents of the ligand with [Cu(MeCN)4][PF6] resulted in a complex in which Cu is coordinated to the three pyrazolyl groups of one ligand and to the P-apex of the other ligand as confirmed by an X-ray crystal structure determination and a DFT computational analysis. Reacting the ligand and the Cu(I) complex in an equimolar ratio resulted in a remarkable one-dimensional P-scorpion coordination polymer for which a single crystal X-ray structure could be determined. A detailed analysis of the structural features is presented.
![Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, 4,9-dichloro-](http://img.cochemist.com/ccimg/848500/848404-06-8.png)
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![Phosphonous dichloride, [2,6-bis(1-methylethyl)phenyl]-](http://img.cochemist.com/ccimg/512900/512803-12-2_b.png)
![Phosphine, (diphenylethenylidene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-](http://img.cochemist.com/ccimg/91500/91425-16-0.png)
![Phosphine, (diphenylethenylidene)[2,4,6-tris(1,1-dimethylethyl)phenyl]-](http://img.cochemist.com/ccimg/91500/91425-16-0_b.png)
![SPIROBI[9H-PYRROLO[1,2-A][1,3]BENZAZASILOLE]](http://img.cochemist.com/ccimg/749300/749253-36-9.png)
![SPIROBI[9H-PYRROLO[1,2-A][1,3]BENZAZASILOLE]](http://img.cochemist.com/ccimg/749300/749253-36-9_b.png)
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![Phosphine oxide, diphenyl[(trimethylsilyl)ethynyl]-](http://img.cochemist.com/ccimg/191600/191597-98-5_b.png)
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![PHOSPHONOUS DICHLORIDE, [2,4,6-TRIS(1-METHYLETHYL)PHENYL]-](http://img.cochemist.com/ccimg/53400/53356-73-3_b.png)
![METHANAMINE, N-5H-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE-](http://img.cochemist.com/ccimg/59900/59864-52-7.png)
![METHANAMINE, N-5H-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE-](http://img.cochemist.com/ccimg/59900/59864-52-7_b.png)
![5H-DIBENZO[A,D]CYCLOHEPTEN-5-AMINE, N-METHYL-](http://img.cochemist.com/ccimg/6500/6476-99-9.png)
![5H-DIBENZO[A,D]CYCLOHEPTEN-5-AMINE, N-METHYL-](http://img.cochemist.com/ccimg/6500/6476-99-9_b.png)
![Propanimidoyl chloride, N-[2,6-bis(1-methylethyl)phenyl]-2,2-dimethyl-](http://img.cochemist.com/ccimg/215800/215715-82-5.png)
![Propanimidoyl chloride, N-[2,6-bis(1-methylethyl)phenyl]-2,2-dimethyl-](http://img.cochemist.com/ccimg/215800/215715-82-5_b.png)
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![PHOSPHONOUS DICHLORIDE, [BIS(TRIMETHYLSILYL)METHYL]-](http://img.cochemist.com/ccimg/76600/76505-20-9_b.png)
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![PHOSPHINE, BIS[3-(TRIFLUOROMETHYL)PHENYL]-](http://img.cochemist.com/ccimg/65800/65796-64-7_b.png)
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![PHOSPHINE, METHYLENE[2,4,6-TRIS(1,1-DIMETHYLETHYL)PHENYL]-](http://img.cochemist.com/ccimg/84200/84114-18-1_b.png)
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![Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]](http://img.cochemist.com/ccimg/12400/12354-85-7_b.png)
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![7,7'-Bidispiro[2.0.2.1]heptane](http://img.cochemist.com/ccimg/395700/395644-53-8_b.png)
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![Spiro[2.2]pentane, methylene-](http://img.cochemist.com/ccimg/19000/18914-34-6_b.png)
![1-[di(pyrazol-1-yl)methyl]pyrazole](http://img.cochemist.com/ccimg/80600/80510-03-8.png)
![1-[di(pyrazol-1-yl)methyl]pyrazole](http://img.cochemist.com/ccimg/80600/80510-03-8_b.png)
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![Tungsten,pentacarbonyl[rel-(1R,2R)-2-[(1S)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874397-83-8_b.png)
![Lithium, [[bis(1,1-dimethylethyl)phosphino]methyl]-](http://img.cochemist.com/ccimg/64100/64065-07-2.png)
![Lithium, [[bis(1,1-dimethylethyl)phosphino]methyl]-](http://img.cochemist.com/ccimg/64100/64065-07-2_b.png)
![Spiro[2.2]pentane, cyclopropylidene-](http://img.cochemist.com/ccimg/50900/50874-23-2.png)
![Spiro[2.2]pentane, cyclopropylidene-](http://img.cochemist.com/ccimg/50900/50874-23-2_b.png)
![Methanamine, N-[[4-(trifluoromethyl)phenyl]methylene]-](http://img.cochemist.com/ccimg/911200/911101-44-5.png)
![Methanamine, N-[[4-(trifluoromethyl)phenyl]methylene]-](http://img.cochemist.com/ccimg/911200/911101-44-5_b.png)
![Tungsten,pentacarbonyl[rel-(1R,2S)-2-[(1S)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874396-83-5.png)
![Tungsten,pentacarbonyl[rel-(1R,2S)-2-[(1S)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874396-83-5_b.png)
![Tungsten,pentacarbonyl[rel-(1R,2R)-2-[(1R)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874396-81-3.png)
![Tungsten,pentacarbonyl[rel-(1R,2R)-2-[(1R)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874396-81-3_b.png)
![Phosphine, [2,4,6-tris(1-methylethyl)phenyl]-](http://img.cochemist.com/ccimg/112500/112438-22-9.png)
![Phosphine, [2,4,6-tris(1-methylethyl)phenyl]-](http://img.cochemist.com/ccimg/112500/112438-22-9_b.png)
![Tungsten,pentacarbonyl[rel-(1R,3R)-1-phenyl-1-phosphadispiro[2.0.2.1]heptane]-](http://img.cochemist.com/ccimg/874400/874337-33-4.png)
![Tungsten,pentacarbonyl[rel-(1R,3R)-1-phenyl-1-phosphadispiro[2.0.2.1]heptane]-](http://img.cochemist.com/ccimg/874400/874337-33-4_b.png)
![Tungsten,pentacarbonyl[rel-(1R,2S)-2-[(1R)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874337-43-6.png)
![Tungsten,pentacarbonyl[rel-(1R,2S)-2-[(1R)-cyclopropylidenecyclopropyl]-1-phenylphosphirane]-](http://img.cochemist.com/ccimg/874400/874337-43-6_b.png)
![Tungsten,pentacarbonyl[rel-(1R,3S,4R)-5-methylene-1-phenyl-1-phosphadispiro[2.0.2.1]heptane]-](http://img.cochemist.com/ccimg/874400/874337-35-6.png)
![Tungsten,pentacarbonyl[rel-(1R,3S,4R)-5-methylene-1-phenyl-1-phosphadispiro[2.0.2.1]heptane]-](http://img.cochemist.com/ccimg/874400/874337-35-6_b.png)
![Phosphine, carbonyl[2,4,6-tris(1,1-dimethylethyl)phenyl]-](http://img.cochemist.com/ccimg/87200/87174-75-2.png)
![Phosphine, carbonyl[2,4,6-tris(1,1-dimethylethyl)phenyl]-](http://img.cochemist.com/ccimg/87200/87174-75-2_b.png)
![5-Chloro-5H-dibenzo[a,d][7]annulene](http://img.cochemist.com/ccimg/18600/18506-04-2.png)
![5-Chloro-5H-dibenzo[a,d][7]annulene](http://img.cochemist.com/ccimg/18600/18506-04-2_b.png)
![Dispiro[2.0.2.1]heptane, 7-cyclopropylidene-](http://img.cochemist.com/ccimg/60600/60538-43-4.png)
![Dispiro[2.0.2.1]heptane, 7-cyclopropylidene-](http://img.cochemist.com/ccimg/60600/60538-43-4_b.png)
![1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE](http://img.cochemist.com/ccimg/7700/7641-77-2.png)
![1,2,3,4,5,6-HEXAMETHYLBICYCLO[2.2.0]HEXA-2,5-DIENE](http://img.cochemist.com/ccimg/7700/7641-77-2_b.png)
![1-BROMO-2-[2-(2-BROMOPHENYL)ETHENYL]BENZENE](http://img.cochemist.com/ccimg/56700/56667-11-9.png)
![1-BROMO-2-[2-(2-BROMOPHENYL)ETHENYL]BENZENE](http://img.cochemist.com/ccimg/56700/56667-11-9_b.png)
![Lithium, [2,4,6-tris(1,1-dimethylethyl)phenyl]-](/data/chemimg/558100/35383-91-6.png)
![Lithium, [2,4,6-tris(1,1-dimethylethyl)phenyl]-](/data/chemimg/558100/35383-91-6_b.png)
![Phosphine, [2,6-bis(1-methylethyl)phenyl]-](http://img.cochemist.com/ccimg/512900/512803-13-3.png)
![Phosphine, [2,6-bis(1-methylethyl)phenyl]-](http://img.cochemist.com/ccimg/512900/512803-13-3_b.png)
![Methanamine,N-[(4-chlorophenyl)methylene]-](http://img.cochemist.com/ccimg/13200/13114-22-2.png)
![Methanamine,N-[(4-chlorophenyl)methylene]-](http://img.cochemist.com/ccimg/13200/13114-22-2_b.png)
![N-[4-(2,2-DIPHENYLETHENYLIDENEAMINO)PHENYL]-2,2-DIPHENYLETHENIMINE](http://img.cochemist.com/ccimg/31300/31201-98-6.png)
![N-[4-(2,2-DIPHENYLETHENYLIDENEAMINO)PHENYL]-2,2-DIPHENYLETHENIMINE](http://img.cochemist.com/ccimg/31300/31201-98-6_b.png)
![Bicyclo[1.1.0]butane](http://img.cochemist.com/ccimg/200/157-33-5.png)
![Bicyclo[1.1.0]butane](http://img.cochemist.com/ccimg/200/157-33-5_b.png)
![Dispiro[2.0.2.1]heptane, 1-methylene-](http://img.cochemist.com/ccimg/50900/50874-26-5.png)
![Dispiro[2.0.2.1]heptane, 1-methylene-](http://img.cochemist.com/ccimg/50900/50874-26-5_b.png)
![[[[AMINO-BIS(TRIMETHYLSILYL)-WEI 5-PHOSPHANYLIDENE]AMINO]-DIMETHYLSILYL]METHANE](http://img.cochemist.com/ccimg/50800/50732-21-3.png)
![[[[AMINO-BIS(TRIMETHYLSILYL)-WEI 5-PHOSPHANYLIDENE]AMINO]-DIMETHYLSILYL]METHANE](http://img.cochemist.com/ccimg/50800/50732-21-3_b.png)
![4,5,9,10-Tetrabromobenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone](/data/chemimg/943148-76-3.png)
![4,5,9,10-Tetrabromobenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone](/data/chemimg/943148-76-3_b.png)
![Dispiro[2.0.2.1]heptane, 7-methylene-](http://img.cochemist.com/ccimg/50900/50874-25-4.png)
![Dispiro[2.0.2.1]heptane, 7-methylene-](http://img.cochemist.com/ccimg/50900/50874-25-4_b.png)
![4,5,9,10-Tetrabromo-2,7-dioctylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone](http://img.cochemist.com/ccimg/954400/954374-43-7.png)
![4,5,9,10-Tetrabromo-2,7-dioctylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone](http://img.cochemist.com/ccimg/954400/954374-43-7_b.png)
![Lithium, (2,2'',4,4'',6,6''-hexamethyl[1,1':3',1''-terphenyl]-2'-yl)-](http://img.cochemist.com/ccimg/164400/164356-88-1.png)
![Lithium, (2,2'',4,4'',6,6''-hexamethyl[1,1':3',1''-terphenyl]-2'-yl)-](http://img.cochemist.com/ccimg/164400/164356-88-1_b.png)
