Co-reporter:Yiping Shi;Paul C. J. Kamer;Michelle Harvie;Emma F. Baxter;Kate J. C. Lim;Peter Pogorzelec
Chemical Science (2010-Present) 2017 vol. 8(Issue 10) pp:6911-6917
Publication Date(Web):2017/09/25
DOI:10.1039/C7SC01718A
The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ε-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2-methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78% yield.
Co-reporter:Patrizia Lorusso;Dr. Jacorien Coetzee;Dr. Graham R. Eastham; David J. Cole-Hamilton
ChemCatChem 2016 Volume 8( Issue 1) pp:222-227
Publication Date(Web):
DOI:10.1002/cctc.201500763
Abstract
A one-pot system for the conversion of methyl propanoate (MeP) to methyl methacrylate (MMA) has been investigated. In particular, this study is focused on the possibility of performing catalytic dehydrogenation of methanol for the in situ production of anhydrous formaldehyde, which is then consumed in a one-pot base-catalysed condensation with MeP to afford methyl 3-hydroxy-2-methylpropanoate, which spontaneously dehydrogenates to MMA, some of which is subsequently hydrogenated to methyl 2-methypropanoate (MiBu).
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Dalton Transactions 2015 vol. 44(Issue 4) pp:1585-1591
Publication Date(Web):08 Dec 2014
DOI:10.1039/C4DT02859G
The utilisation of the PNP iridium pincer complex [Ir(PNP)(COE)][BF4] [PNP = 2,6-bis{(di-tert-butylphosphino)methyl}pyridine; COE = cyclooctene] in the sp3 C–H activation of methyl propanoate and other related esters was explored. In particular, this study provides further insight into the factors that govern the regioselectivity of such reactions. These included factors such as the steric demands of the substrate, the formation of favourable ring systems as well as the electronic effects that may influence the pKa values of protons. In particular, the effects of water on the outcome of these reactions were of great interest, since earlier literature reports have shown the presence of water to promote selective C–H activation in the α-position of ketones.
Co-reporter:Cristina Jiménez-Rodriguez, Angel A. Núñez-Magro, Thomas Seidensticker, Graham R. Eastham, Marc R. L. Furst and David J. Cole-Hamilton
Catalysis Science & Technology 2014 vol. 4(Issue 8) pp:2332-2339
Publication Date(Web):16 Apr 2014
DOI:10.1039/C4CY00158C
The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω-ester amides, whilst reactions in THF give N-phenylpyrrolidine.
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Dalton Transactions 2014 vol. 43(Issue 9) pp:3479-3491
Publication Date(Web):03 Jan 2014
DOI:10.1039/C3DT52552J
The coordination chemistry and solution behaviour of Rh(I) and Ru(II) complexes derived from mixed anhydride ligands of carboxylic acids and phosphorus acids were explored. Similar to the free ligand systems, mixed anhydride complexes rearranged in solution via a number of pathways, with the pathway of choice dependent on the mixed anhydride employed, the auxiliary ligands present as well as the nature of the metal centre. Plausible mechanisms for some of the routes of rearrangement and by-product formation are proposed. Where stability allowed, new complexes were fully characterised, including solid state structures for four of the unrearranged mixed anhydride complexes and two of the interesting rearrangement products.
Co-reporter:Marc R. L. Furst, Thomas Seidensticker and David J. Cole-Hamilton
Green Chemistry 2013 vol. 15(Issue 5) pp:1218-1225
Publication Date(Web):22 Feb 2013
DOI:10.1039/C3GC37071B
Tall Oil Fatty Acids, a low value side product from the paper industry containing mainly oleic and linoleic acids, are used for producing the polyester precursor, dimethyl 1,19-nonadecanedioate by methoxycarbonylation in the presence of [Pd2(dba)3], 1,2-bis(ditertiarybutylphosphinomethyl)benzene and methanesulfonic acid in methanol. The methoxycarbonylation of methyl linoleate has been used to identify other products formed and approaches to their minimisation have been developed. It has also been used for the production of trimethyl heptadecanetricarboxylates. Finally, conjugated unsaturated esters of different chain length (up to 16 C atoms), some of them available from plant oils, are subjected to methoxycarbonylation to give α,ω-diesters.
Co-reporter:Dr. Jacorien Coetzee;Dr. Deborah L. Dodds; Jürgen Klankermayer;Sra Brosinski; Walter Leitner; Alexra M. Z. Slawin; David J. Cole-Hamilton
Chemistry - A European Journal 2013 Volume 19( Issue 33) pp:11039-11050
Publication Date(Web):
DOI:10.1002/chem.201204270
Abstract
Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4-pentanedione), triphos [1,1,1-tris- (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and the mechanism of the reaction, a range of methanesulfonato complexes has been prepared from [Ru(acac)3], triphos and MSA, or from reactions of [RuX(OAc)(triphos)] (X=H or OAc) or [RuH2(CO)(triphos)] with MSA. Crystallographically characterised complexes include: [Ru(OAc-κ1O)2(H2O)(triphos)], [Ru(OAc-κ2O,O′)(CH3SO3-κ1O)(triphos)], [Ru(CH3SO3-κ1O)2(H2O)(triphos)] and [Ru2(μ-CH3SO3)3(triphos)2][CH3SO3], whereas other complexes, such as [Ru(OAc-κ1O)(OAc-κ2O,O′)(triphos)], [Ru(CH3SO3-κ1O)(CH3SO3-κ2O,O′)(triphos)], H[Ru(CH3SO3-κ1O)3(triphos)], [RuH(CH3SO3-κ1O)(CO)(triphos)] and [RuH(CH3SO3-κ2O,O′)(triphos)] have been characterised spectroscopically. The interactions between these various complexes and their relevance to the catalytic reactions are discussed.
Co-reporter:Dr. Jacorien Coetzee;Dr. Haresh G. Manyar;Dr. Christopher Hardacre;Dr. David J. Cole-Hamilton
ChemCatChem 2013 Volume 5( Issue 10) pp:2843-2847
Publication Date(Web):
DOI:10.1002/cctc.201300431
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 18) pp:3677-3688
Publication Date(Web):05 Mar 2012
DOI:10.1039/C2OB07164A
Simple mixed anhydrides are known to pose synthetic difficulties relating to their thermal lability and ways to stabilise such mixed anhydride systems by relying on either electronic or steric effects were therefore explored. Thus, a series of acyloxyphosphines and acylphosphites derived from either propanoic acid or phenylacetic acid were prepared and their in solution stability assessed. These compounds were, where stability allowed, fully characterised using standard analytical techniques. NMR studies, in particular, unearthed interesting coupling behaviour for a number of the acyloxyphosphines and acylphosphites as well as their rearrangement products which could be linked to their chiral nature. Furthermore, the crystal structures for three of the prepared mixed anhydrides were determined using X-ray crystallography and are reported herein.
Co-reporter:Simon L. Desset, Simon W. Reader and David J. Cole-Hamilton
Green Chemistry 2009 vol. 11(Issue 5) pp:630-637
Publication Date(Web):06 Mar 2009
DOI:10.1039/B822139A
The aqueous-biphasic hydroformylation of higher alkenes catalyzed by Rh/TPPTS has been carried out in the presence of imidazolium, pyridinium and triethylammonium salts. High reaction rates are achieved with imidazolium and triethylammonium salts provided that their alkyl “tail” is ≥C8. Fast and complete phase separation, and good retention of the metal in the aqueous phase could be achieved with an octyl “tail”. Imidazolium salts were found to give the highest rate enhancement. The nature of the anion showed a moderate influence on the reaction. Evidence suggests that the additive can act as weak surfactant allowing emulsions to be formed and broken by simply switching the stirring on and off.
Co-reporter:Nicolas R. Vautravers, Pascal André and David J. Cole-Hamilton
Journal of Materials Chemistry A 2009 vol. 19(Issue 26) pp:4545-4550
Publication Date(Web):18 May 2009
DOI:10.1039/B818060A
A polyhedral oligomeric silsesquioxane (POSS) has been decorated with eight peripheral 4′-vinylbiphenyl-3,5-dicarbaldehyde groups. Although this macromolecule is not fluorescent, reducing agents such as NaBH4 and LiAlH4 activate its fluorescence by turning the aldehydic functions into primary alcohols. Molecular dynamics calculations demonstrated similar spherical structures for both macromolecules regardless of whether the terminal functions were aldehyde or alcohol.
Co-reporter:Murielle F. Sellin, Ingrid Bach, Jeremy M. Webster, Francisco Montilla, Vitor Rosa, Teresa Avilés, Martyn Poliakoff and David J. Cole-Hamilton
Dalton Transactions 2002 (Issue 24) pp:4569-4576
Publication Date(Web):18 Nov 2002
DOI:10.1039/B207747G
Rhodium complexes modified by simple trialkylphosphines can be used to carry out homogeneous hydroformylation in supercritical carbon dioxide (scCO2). The catalyst derived from PEt3 is more active and slightly more selective for the linear products in scCO2 than in toluene, and under the same reaction conditions [100°C, 40 bar of CO/H2
(1∶1)] P(OPri)3 is also an effective ligand giving good catalyst solubility and activity. Other ligands such as PPh3, POct3, PCy3, and P(4-C6H4But)3 are less effective because of the low solubility of their rhodium complexes in scCO2. P(4-C6H4SiMe3)nPh3−n (n = 3 or 1) and P(OPh)3 impart activity despite their complexes only being poorly soluble in scCO2. Under subcritical conditions, using PEt3 as the ligand, C7-alcohols from hydrogenation of the first formed aldehydes are the main products whilst above a total pressure of 200 bar, where the solution remains supercritical (monophasic) throughout the reaction, aldehydes are obtained with 97% selectivity. High pressure IR studies in scCO2 using PEt3 as the ligand are reported.
Co-reporter:Loı̈c Ropartz, Russell E. Morris, Douglas F. Foster, David J. Cole-Hamilton
Journal of Molecular Catalysis A: Chemical 2002 Volumes 182–183() pp:99-105
Publication Date(Web):31 May 2002
DOI:10.1016/S1381-1169(01)00502-7
Radical additions of diethyl- and diphenylphosphine have been used to prepare 1st and 2nd generation dendrimers based on polyhedral oligosilsesquioxane cores by a divergent synthetic method. The 1st generation dendrimer is built on either 16 and 24 vinyl or allyl arms formed by successive hydrosilation and vinylation or allylation of vinyl-functionalised polyhedral silsesquioxanes. Successive hydrosilation/allylation followed by hydrosilation/vinylation and addition of phosphine produce the 2nd generation dendrimer. The dendrimers have been used as ligands for the hydroformylation of oct-1-ene catalysed by [Rh(acac)(CO)2]. Using the alkylphosphine-containing dendrimers as ligands, alcohols (nonan-1-ol and 2-methyloctanol) are obtained, whilst the diphenylphosphine counterparts lead to the formation of aldehydes (nonan-1-al and 2-methyloctanal). Linear to branched ratios of 3/1 are obtained for the diethylphosphine compounds while ratios of 12 to 14/1 are given by the diphenylphosphine dendritic molecules.
Co-reporter:Nicolas R. Vautravers, Pascal André and David J. Cole-Hamilton
Journal of Materials Chemistry A 2009 - vol. 19(Issue 26) pp:NaN4550-4550
Publication Date(Web):2009/05/18
DOI:10.1039/B818060A
A polyhedral oligomeric silsesquioxane (POSS) has been decorated with eight peripheral 4′-vinylbiphenyl-3,5-dicarbaldehyde groups. Although this macromolecule is not fluorescent, reducing agents such as NaBH4 and LiAlH4 activate its fluorescence by turning the aldehydic functions into primary alcohols. Molecular dynamics calculations demonstrated similar spherical structures for both macromolecules regardless of whether the terminal functions were aldehyde or alcohol.
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Dalton Transactions 2015 - vol. 44(Issue 4) pp:NaN1591-1591
Publication Date(Web):2014/12/08
DOI:10.1039/C4DT02859G
The utilisation of the PNP iridium pincer complex [Ir(PNP)(COE)][BF4] [PNP = 2,6-bis{(di-tert-butylphosphino)methyl}pyridine; COE = cyclooctene] in the sp3 C–H activation of methyl propanoate and other related esters was explored. In particular, this study provides further insight into the factors that govern the regioselectivity of such reactions. These included factors such as the steric demands of the substrate, the formation of favourable ring systems as well as the electronic effects that may influence the pKa values of protons. In particular, the effects of water on the outcome of these reactions were of great interest, since earlier literature reports have shown the presence of water to promote selective C–H activation in the α-position of ketones.
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Dalton Transactions 2014 - vol. 43(Issue 9) pp:NaN3491-3491
Publication Date(Web):2014/01/03
DOI:10.1039/C3DT52552J
The coordination chemistry and solution behaviour of Rh(I) and Ru(II) complexes derived from mixed anhydride ligands of carboxylic acids and phosphorus acids were explored. Similar to the free ligand systems, mixed anhydride complexes rearranged in solution via a number of pathways, with the pathway of choice dependent on the mixed anhydride employed, the auxiliary ligands present as well as the nature of the metal centre. Plausible mechanisms for some of the routes of rearrangement and by-product formation are proposed. Where stability allowed, new complexes were fully characterised, including solid state structures for four of the unrearranged mixed anhydride complexes and two of the interesting rearrangement products.
Co-reporter:Jacorien Coetzee, Graham R. Eastham, Alexandra M. Z. Slawin and David J. Cole-Hamilton
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 18) pp:NaN3688-3688
Publication Date(Web):2012/03/05
DOI:10.1039/C2OB07164A
Simple mixed anhydrides are known to pose synthetic difficulties relating to their thermal lability and ways to stabilise such mixed anhydride systems by relying on either electronic or steric effects were therefore explored. Thus, a series of acyloxyphosphines and acylphosphites derived from either propanoic acid or phenylacetic acid were prepared and their in solution stability assessed. These compounds were, where stability allowed, fully characterised using standard analytical techniques. NMR studies, in particular, unearthed interesting coupling behaviour for a number of the acyloxyphosphines and acylphosphites as well as their rearrangement products which could be linked to their chiral nature. Furthermore, the crystal structures for three of the prepared mixed anhydrides were determined using X-ray crystallography and are reported herein.
Co-reporter:Cristina Jiménez-Rodriguez, Angel A. Núñez-Magro, Thomas Seidensticker, Graham R. Eastham, Marc R. L. Furst and David J. Cole-Hamilton
Catalysis Science & Technology (2011-Present) 2014 - vol. 4(Issue 8) pp:NaN2339-2339
Publication Date(Web):2014/04/16
DOI:10.1039/C4CY00158C
The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω-ester amides, whilst reactions in THF give N-phenylpyrrolidine.
![7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (1S,4S,6R)-](http://img.cochemist.com/ccimg/32600/32543-51-4.png)
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![Spiro[2.4]hepta-4,6-diene, 4,5,6,7-tetramethyl-](http://img.cochemist.com/ccimg/198400/198331-54-3.png)
![Spiro[2.4]hepta-4,6-diene, 4,5,6,7-tetramethyl-](http://img.cochemist.com/ccimg/198400/198331-54-3_b.png)
![PHOSPHINE, [1,2-PHENYLENEBIS(METHYLENE)]BIS[BIS(1-METHYLETHYL)-](http://img.cochemist.com/ccimg/850400/850318-11-5.png)
![PHOSPHINE, [1,2-PHENYLENEBIS(METHYLENE)]BIS[BIS(1-METHYLETHYL)-](http://img.cochemist.com/ccimg/850400/850318-11-5_b.png)
![Phosphine, [(dimethylsilylene)di-2,1-ethanediyl]bis[diphenyl-](http://img.cochemist.com/ccimg/76800/76734-23-1.png)
![Phosphine, [(dimethylsilylene)di-2,1-ethanediyl]bis[diphenyl-](http://img.cochemist.com/ccimg/76800/76734-23-1_b.png)
![Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]](http://img.cochemist.com/ccimg/12400/12354-85-7.png)
![Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]](http://img.cochemist.com/ccimg/12400/12354-85-7_b.png)
![Pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane,1,3,5,7,9,11,13,15-octakis[2-(trichlorosilyl)ethyl]-](http://img.cochemist.com/ccimg/214700/214675-88-4.png)
![Pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane,1,3,5,7,9,11,13,15-octakis[2-(trichlorosilyl)ethyl]-](http://img.cochemist.com/ccimg/214700/214675-88-4_b.png)
![Lithium, [(dimethylphosphino)methyl]-](http://img.cochemist.com/ccimg/64100/64065-06-1.png)
![Lithium, [(dimethylphosphino)methyl]-](http://img.cochemist.com/ccimg/64100/64065-06-1_b.png)
![Pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane,1,3,5,7,9,11,13,15-octakis[2-(chlorodimethylsilyl)ethyl]-](http://img.cochemist.com/ccimg/243200/243146-51-2.png)
![Pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane,1,3,5,7,9,11,13,15-octakis[2-(chlorodimethylsilyl)ethyl]-](http://img.cochemist.com/ccimg/243200/243146-51-2_b.png)
![6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine](http://img.cochemist.com/ccimg/16700/16611-68-0.png)
![6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine](http://img.cochemist.com/ccimg/16700/16611-68-0_b.png)
![7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-](http://img.cochemist.com/ccimg/1200/1195-92-2.png)
![7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-](http://img.cochemist.com/ccimg/1200/1195-92-2_b.png)
![3-[(8Z)-pentadec-8-en-1-yl]phenol](http://img.cochemist.com/ccimg/600/501-26-8.png)
![3-[(8Z)-pentadec-8-en-1-yl]phenol](http://img.cochemist.com/ccimg/600/501-26-8_b.png)
![Phosphine,tris[4-(trimethylsilyl)phenyl]-](http://img.cochemist.com/ccimg/18900/18848-96-9.png)
![Phosphine,tris[4-(trimethylsilyl)phenyl]-](http://img.cochemist.com/ccimg/18900/18848-96-9_b.png)
![Molybdenum,tetracarbonyl[1,2-ethanediylbis[diphenylphosphine-kP]]-, (OC-6-22)-](http://img.cochemist.com/ccimg/15500/15444-66-3.png)
![Molybdenum,tetracarbonyl[1,2-ethanediylbis[diphenylphosphine-kP]]-, (OC-6-22)-](http://img.cochemist.com/ccimg/15500/15444-66-3_b.png)
![7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(1-methylethenyl)-, (1S,4R,6R)-](http://img.cochemist.com/ccimg/7000/6909-30-4.png)
![7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(1-methylethenyl)-, (1S,4R,6R)-](http://img.cochemist.com/ccimg/7000/6909-30-4_b.png)
![Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]]](http://img.cochemist.com/ccimg/26200/26161-42-2.png)
![Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]]](http://img.cochemist.com/ccimg/26200/26161-42-2_b.png)
![Lithium,[4-(dimethylamino)phenyl]-](http://img.cochemist.com/ccimg/13200/13190-50-6.png)
![Lithium,[4-(dimethylamino)phenyl]-](http://img.cochemist.com/ccimg/13200/13190-50-6_b.png)
![SPIRO[2.4]HEPTA-4,6-DIENE](http://img.cochemist.com/ccimg/800/765-46-8.png)
![SPIRO[2.4]HEPTA-4,6-DIENE](http://img.cochemist.com/ccimg/800/765-46-8_b.png)
![Tungstate(3-),tetracosa-m-oxododecaoxo[m12-[phosphato(3-)-kO:kO:kO:kO':kO':kO':kO'':kO'':kO'':kO''':kO''':kO''']]dodeca-,hydrogen (1:3)](http://img.cochemist.com/ccimg/1400/1343-93-7.png)
![Tungstate(3-),tetracosa-m-oxododecaoxo[m12-[phosphato(3-)-kO:kO:kO:kO':kO':kO':kO'':kO'':kO'':kO''':kO''':kO''']]dodeca-,hydrogen (1:3)](http://img.cochemist.com/ccimg/1400/1343-93-7_b.png)
![(1R,4R,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane](http://img.cochemist.com/ccimg/13900/13837-75-7.png)
![(1R,4R,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane](http://img.cochemist.com/ccimg/13900/13837-75-7_b.png)
![Phosphine,tris[4-(tridecafluorohexyl)phenyl]-](http://img.cochemist.com/ccimg/193200/193197-68-1.png)
![Phosphine,tris[4-(tridecafluorohexyl)phenyl]-](http://img.cochemist.com/ccimg/193200/193197-68-1_b.png)
![Lithium, [(diphenylphosphino)methyl]-](http://img.cochemist.com/ccimg/62300/62263-69-8.png)
![Lithium, [(diphenylphosphino)methyl]-](http://img.cochemist.com/ccimg/62300/62263-69-8_b.png)
![2-METHYL-2-PROPANYL {[1-(HYDROXYMETHYL)CYCLOPROPYL]METHYL}CARBAMA<WBR />TE](http://img.cochemist.com/ccimg/34200/34172-60-6.png)
![2-METHYL-2-PROPANYL {[1-(HYDROXYMETHYL)CYCLOPROPYL]METHYL}CARBAMA<WBR />TE](http://img.cochemist.com/ccimg/34200/34172-60-6_b.png)
![Benzenamine,N-[(4-methylphenyl)methylene]-](http://img.cochemist.com/ccimg/2400/2362-77-8.png)
![Benzenamine,N-[(4-methylphenyl)methylene]-](http://img.cochemist.com/ccimg/2400/2362-77-8_b.png)
