Draganjac, Mark

Muthyala, S.

UARK (University of Arkansas )

Journal of the Arkansas Academy of Science Volume 67 Article 36 2013 Microwave Assisted Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II) S. Muthyala Arkansas State University Mark Draganjac Arkansas State University, mdraganj@astate.edu Follow this and additional works at: https://scholarworks.uark.edu/jaas  Part of the Inorganic Chemistry Commons, and the Organic Chemistry Commons Recommended Citation Muthyala, S. and Draganjac, Mark (2013) "Microwave Assisted Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)," Journal of the Arkansas Academy of Science: Vol. 67 , Article 36. DOI: https://doi.org/10.54119/jaas.2013.6731 Available at: https://scholarworks.uark.edu/jaas/vol67/iss1/36 This article is available for use under the Creative Commons license: Attribution-NoDerivatives 4.0 International (CC BY-ND 4.0). Users are able to read, download, copy, print, distribute, search, link to the full texts of these articles, or use them for any other lawful purpose, without asking prior permission from the publisher or the author. This General Note is brought to you for free and open access by ScholarWorks@UARK. It has been accepted for inclusion in Journal of the Arkansas Academy of Science by an authorized editor of ScholarWorks@UARK. For more information, please contact scholar@uark.edu. Journal of the Arkansas Academy of Science, Vol. 67, 2013204Microwave Assisted Synthesis ofChloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)S. Muthyala, and M. Draganjac*Department of Chemistry and Physics, Arkansas State University, State University, AR 72467*Correspondence: mdraganj@astate.eduRunning Title: Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)Microwave-assisted syntheses have beenimplemented in the preparation of both organic andinorganic compounds. Advantages include increasedyields and faster reaction times (Kingston and Haswell1997). In ruthenium chemistry, Greene and Mingosfirst used microwave technology to prepare a series ofRu(II)-bipyridine complexes in the early 90’s (Greeneand Mingos 1991). Several polypyridine complexeshave since been prepared using microwaves(Matsumura-Inoue et al. 1994, Anderson et al. 2006).The Ru(dmso)4Cl2 complex has been synthesized usingopen vessel (Sun et al. 2010) and closed vessel(Harvey et al. 2009) reactions. Other examples ofmicrowave-assisted syntheses include the preparationof ruthenium-thiosemicarbazone complexes (Beckfordet al. 2009) and ruthenium-tris(pyrazolyl)boratesandwich complexes (Zagermann et al. 2011).A useful starting material for the preparation ofnew ruthenium-containing complexes isCpRu(dppe)Cl. Chloride substitution reactions haveresulted in the formation of compounds of generalform CpRu(dppe)L, where L = polyalkynes (Bruce etal. 2012), carbenes (Bowie et al. 2012), P4 (Di Vaira etal. 2006), carborane (Basato et al. 2007), thiol(Treichel et al. 1991, Shaw et al. 2007), thiolate (Shawet al. 2007, Shawakfeh et al. 2008) and stannic halides(de Moura et al. 2003) to name a few.The CpRu(dppe)Cl compound is synthesized byrefluxing CpRu(PPh3)2Cl and 1,2-bis(diphenyl-phosphino)ethane in benzene, followed by reduction ofvolume and subsequent precipitation of the product bya 4/1 ethyl ether/hexane mixture (Ashby et al. 1979).This reaction involves a reflux of 8 hours and anadditional 10 hours for precipitating the final product.Reduction in volume is also critical, as too littlereduction leads to reduced yields. The length ofreaction time and the difficulties in preparing thisproduct have led us to explore the use of microwaveirradiation for improving the preparation ofCpRu(dppe)Cl.Microwave-assisted synthesis of CpRu(dppe)Clwas performed using a CEM Discover microwavereactor. Solvents were obtained from Fisher Scientificand were used as received without further purification.ACS-grade chloroform-d stored over molecular sieveswas used as a solvent for NMR. 1H NMR of theproducts was carried out using a Bruker Topspin 300-MHz NMR. A Buchi rotary evaporator was used forconcentrating the reaction mixtures. The startingmaterial, CpRu(PPh3)2Cl, was prepared as described inthe literature (Ashby et al. 1979) for comparison of thetwo reactions.For the microwave reaction, 0.050g (0.069 mmol)of CpRu(PPh3)2Cl and 0.027g (0.069 mmol) of 1,2-bis(diphenylphosphino)ethane were dissolved in 2 mLof toluene in a reaction tube. A stir bar was added,nitrogen gas was bubbled into the tubes for one minutebefore setting them in the microwave reactor. Once thereaction was completed, the reaction mixtures weretransferred into a 50-mL round-bottom flask and wereconcentrated using a rotary evaporator until thereaction-mixture volume was approximately 1mL. Tothe round-bottom flask, 25 mL of 4/1 ethylether/hexane mixture was added and was allowed tocool to 0 oC overnight. The yellow precipitate thatformed overnight was filtered. To the filtrate,approximately 13 mL of hexane was added. Orangeprecipitate that formed was filtered and washed with4/1 ethyl ether/hexane mixture and dried. Yield = 32%. Product was characterized by 1H NMR. ( , CDCl3,ppm: 7.3, 7.9, m, 20H, phenyl groups; 4.55, s, 5H,C5H5; 2.5, m, 4H, -CH2-).In order to study the effect of reaction parameterson product yield, reaction parameters such as holdtime, ramp time and temperature was varied. In atypical reaction involving change in hold time,reactions were performed for 5 minutes, 6 minutes, 7minutes and 8 minutes. Temperature was kept constantat 95 oC for all the reactions. Results from thesereactions are shown in Table 1.A second set of reactions was performed byvarying the temperature of the microwave reactor.204Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36Published by Arkansas Academy of Science, 2013Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)Journal of the Arkansas Academy of Science, Vol. 67, 2013205Reactions were performed at 95, 85, 80 and 70 oC. Thehold time was kept constant at 5 minutes. Results fromthese reactions are shown in Table 2. For the last twotrials with a reaction temperature of either 80 or 70 oC,pure product was not obtained; therefore, no yield wasreported.Table 1: Reaction parameters and yields from holdtime trialsHoldtime(min)T( oC)Ramptime(min)Actualyield(g)%yield5 95 10 0.012 306 95 12 0.004 107 95 14 0.006 208 95 16 0.008 20Table 2: Reaction parameters and yields fromtemperature trialsT(oC)Holdtime(min)Ramptime(min)Actualyield(g)%yield95 5 10 0.013 32.85 5 10 0.009 2080 5 10 No yield No yield70 5 10 No yield No yieldThe last set of reactions was performed by varyingthe ramp time. Reactions were performed for 7minutes, 8 minutes, 9 minutes and 10 minutes. Thehold time was kept constant at 5 minutes, and thetemperature was maintained at 95 oC. Results fromthese reactions are shown in Table 3.From the trials performed by varying reactionparameters, the reaction performed for a ramp time of8 minutes and a hold time of 5 minutes at 95 oC gavethe highest yield (38%). Setup time for microwavereactions is 10 minutes, and the reactions take as longas 5-10 minutes for each tube, so overall time for thereaction is 15-20 minutes for each reaction tube. It wasnoticed that yields from multiple reaction tubes rangedfrom a low of 2.5% to a maximum of 37%, whichTable 3: Reaction parameters and yields from ramptime trialsRamptime(min)T( oC)Holdtime(min)Actualyield(g)%yield10 95 5 0.012 309 95 5 0.009 208 95 5 0.015 387 95 5 0.006 20meant that several tubes had to be prepared to get therequired gram amounts necessary for further reactions.By comparison, the set up time for the reaction usingconventional heating is less than 10 minutes, butinvolves a longer reaction time (15-16 hours). Theyield obtained from this reaction (80 %, Ashby et al.1979) is approximately equal to yields obtained from 5microwave reaction tubes combined.Better yields are achieved by conventional heatingcompared to our microwave synthesis. The microwavesynthesis results in a decrease in reaction time. Thus, iftime is a factor, microwave synthesis is a better methodfor synthesizing CpRu(dppe)Cl, whereas if higheryields are required, conventional heating is a bettermethod for synthesizing CpRu(dppe)Cl.In conclusion, microwave-assisted synthesis can beutilized for the preparation of CpRu(dppe)Cl, but thepoor yields and difficulty in purifying the reactionproduct makes the conventional literature preparation(Ashby et al. 1979) the preferred synthetic techniquefor the preparation of CpRu(dppe)Cl.AcknowledgmentsThe authors thank Arkansas State University andthe Department of Chemistry and Physics for theirsupport of this project.Literature CitedAnderson TJ, JR Scott, F Millett and B Durham.2006. Decarboxylation of 2,2’-bipyridinyl-4,4’-dicarboxylic acid diethyl ester during microwavesynthesis of the correspondiong trichelatedruthenium complex. Inorganic Chemistry45:3843-3845.205Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36https://scholarworks.uark.edu/jaas/vol67/iss1/36DOI: https://doi.org/10.54119/jaas.2013.6731S. Muthyala and M. DraganjacJournal of the Arkansas Academy of Science, Vol. 67, 2013206Ashby GS, MI Bruce, IB Tomkins and RC Wallis.1979. Cyclopentadienyl-ruthenium and osmiumchemistry. VII. Complexes containing nitriles,tertiary phosphines or phosphites formed byaddition or displacement reactions. AustralianJournal of Chemistry 32:1003-1016.Basato M, A Biffis, G Buscemi, E Callegaro,M Polo, C Tubaro, A Venso, et al. 2007.Reaction of cyclopentadienyl ruthenium complexeswith a carborane anion: effect of the spectatorligands on the substitution site. Organometallics26:4265-4270.Beckford FA, M Shaloski, G Leblanc, J Thessing,LC Lewis-Alleyne, AA Holder, L Li and NPSeeram. 2003. Microwave synthesis of mixedligand diimine-thiosemicarbazone complexes ofruthenium(II): biophysical reactivity andcytotoxicity. Dalton Transactions 2003:10757-10764.Bowie JH, MI Bruce, MA Buntine, AS Gentleman,DC Graham, PJ Low, GF Metha, et al. 2012.Facile decarboxylation of propiolic acid on aruthenium center and related chemistry.Organometallics 31:5262-5273.Bruce MI, K Costuas, F Gendron, J-F Halet,M Jevric and BW Skelton. 2012. Oxidativedimerization of aryldiynyl-ruthenium complexes.Organometallics 31: 6555-6566.de Moura EM, HGL Siebald, GM de Lima,OA Porto, CV Rodarte de Moura and MHorner. 2003. The synthesis and structuralcharacterization of Ru-Sn based derivativesbearing asymmetric X2ClSn- (X= Br and F) anions.Journal of Molecular Structure 658:71-78.di Vaira M, M Peruzzini, SS Costantini andP Stoppioni. 2006. Hydrolytic disproportionationof coordinated white phosphorus in[CpRu(dppe)( 1-P4)]PF6 [dppe = 1,2-bis(diphenylphosphino)-ethane]. Journal ofOrganometallic Chemistry 691:3931-3937.Greene DL and DMP Mingos. 1991. Application ofmicrowave dielectric loss heating effects for therapid and convenient synthesis of ruthenium(II)polypyridine complexes. Transition MetalChemistry 16:71-72.Harvey A, M Draganjac, S Chui, R Snell, andE Benjamin. 2009. Microwave Synthesis of cis-Dichlorotetrakis(dimethylsulfoxide)ruthenium(II).Journal of the Arkansas Academy of Science63:185.Kingston HM and SJ Haswell (eds.). 1997.Microwave-enhanced chemistry: fundamentalssample preparation and application. Washington,DC: American Chemical Society. 772.Matsumura-Inoue T, M Tanabe, T Minami andT Ohashi. 1994. A remarkably rapid synthesis ofruthenium(II) polypyridine complexes bymicrowave irradiation. Chemistry Letters1994:2443-2446.Shaw AP, BL Ryland, JR Norton, D Buccella andA Moscatelli. 2007. Electron exchange involving asulfur-stabilized ruthenium radical cation.Inorganic Chemistry 46:5805-5812.Shawakfeh K, M El-khateeb, D Taher, H Gorls andW Weigand. 2008. Half-sandwich rutheniumcomplexes of pentafluorobenzenethiolato ligands.Transition Metal Chemistry 33:387-391.Sun Y, ML Machala and FN Castellano. 2010.Controlled microwave synthesis of Ru(II) synthonsand chromophores relevant to solar energyconversion. Inorganica Chimica Acta 363:283-287.Treichel PM, MS Schmidt and RA Crane. 1991.Synthesis of new cyclopentadienyliron and -ruthenium benzenethiolate, thiol, and thio ethercomplexes. Inorganic Chemistry 30:379-81.Zagermann J, M Mariusz and N Metzler-Nolte.2011. Microwave-assisted synthesis of the Tpsandwich compound TpRu(p-Br-C6H4Tp) andapplication of its benzoic acid derivative TpRu(p-CO2H-C6H4Tp) in the covalent labeling ofbiomolecules. Dalton Transactions 2011:1011-1015.206Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36Published by Arkansas Academy of Science, 2013

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Microwave Assisted Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)

ScholarWorks@UARK

Journal of the Arkansas Academy of ScienceVolume 67 Article 362013Microwave Assisted Synthesis ofChloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)S. MuthyalaArkansas State UniversityMark DraganjacArkansas State University, mdraganj@astate.eduFollow this and additional works at: http://scholarworks.uark.edu/jaasPart of the Inorganic Chemistry Commons, and the Organic Chemistry CommonsThis article is available for use under the Creative Commons license: Attribution-NoDerivatives 4.0 International (CC BY-ND 4.0). Users are able toread, download, copy, print, distribute, search, link to the full texts of these articles, or use them for any other lawful purpose, without asking priorpermission from the publisher or the author.This General Note is brought to you for free and open access by ScholarWorks@UARK. It has been accepted for inclusion in Journal of the ArkansasAcademy of Science by an authorized editor of ScholarWorks@UARK. For more information, please contact scholar@uark.edu.Recommended CitationMuthyala, S. and Draganjac, Mark (2013) "Microwave Assisted Synthesis ofChloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)," Journal of the Arkansas Academy of Science: Vol. 67 ,Article 36.Available at: http://scholarworks.uark.edu/jaas/vol67/iss1/36Journal of the Arkansas Academy of Science, Vol. 67, 2013204Microwave Assisted Synthesis ofChloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)S. Muthyala, and M. Draganjac*Department of Chemistry and Physics, Arkansas State University, State University, AR 72467*Correspondence: mdraganj@astate.eduRunning Title: Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)Microwave-assisted syntheses have beenimplemented in the preparation of both organic andinorganic compounds. Advantages include increasedyields and faster reaction times (Kingston and Haswell1997). In ruthenium chemistry, Greene and Mingosfirst used microwave technology to prepare a series ofRu(II)-bipyridine complexes in the early 90’s (Greeneand Mingos 1991). Several polypyridine complexeshave since been prepared using microwaves(Matsumura-Inoue et al. 1994, Anderson et al. 2006).The Ru(dmso)4Cl2 complex has been synthesized usingopen vessel (Sun et al. 2010) and closed vessel(Harvey et al. 2009) reactions. Other examples ofmicrowave-assisted syntheses include the preparationof ruthenium-thiosemicarbazone complexes (Beckfordet al. 2009) and ruthenium-tris(pyrazolyl)boratesandwich complexes (Zagermann et al. 2011).A useful starting material for the preparation ofnew ruthenium-containing complexes isCpRu(dppe)Cl. Chloride substitution reactions haveresulted in the formation of compounds of generalform CpRu(dppe)L, where L = polyalkynes (Bruce etal. 2012), carbenes (Bowie et al. 2012), P4 (Di Vaira etal. 2006), carborane (Basato et al. 2007), thiol(Treichel et al. 1991, Shaw et al. 2007), thiolate (Shawet al. 2007, Shawakfeh et al. 2008) and stannic halides(de Moura et al. 2003) to name a few.The CpRu(dppe)Cl compound is synthesized byrefluxing CpRu(PPh3)2Cl and 1,2-bis(diphenyl-phosphino)ethane in benzene, followed by reduction ofvolume and subsequent precipitation of the product bya 4/1 ethyl ether/hexane mixture (Ashby et al. 1979).This reaction involves a reflux of 8 hours and anadditional 10 hours for precipitating the final product.Reduction in volume is also critical, as too littlereduction leads to reduced yields. The length ofreaction time and the difficulties in preparing thisproduct have led us to explore the use of microwaveirradiation for improving the preparation ofCpRu(dppe)Cl.Microwave-assisted synthesis of CpRu(dppe)Clwas performed using a CEM Discover microwavereactor. Solvents were obtained from Fisher Scientificand were used as received without further purification.ACS-grade chloroform-d stored over molecular sieveswas used as a solvent for NMR. 1H NMR of theproducts was carried out using a Bruker Topspin 300-MHz NMR. A Buchi rotary evaporator was used forconcentrating the reaction mixtures. The startingmaterial, CpRu(PPh3)2Cl, was prepared as described inthe literature (Ashby et al. 1979) for comparison of thetwo reactions.For the microwave reaction, 0.050g (0.069 mmol)of CpRu(PPh3)2Cl and 0.027g (0.069 mmol) of 1,2-bis(diphenylphosphino)ethane were dissolved in 2 mLof toluene in a reaction tube. A stir bar was added,nitrogen gas was bubbled into the tubes for one minutebefore setting them in the microwave reactor. Once thereaction was completed, the reaction mixtures weretransferred into a 50-mL round-bottom flask and wereconcentrated using a rotary evaporator until thereaction-mixture volume was approximately 1mL. Tothe round-bottom flask, 25 mL of 4/1 ethylether/hexane mixture was added and was allowed tocool to 0 oC overnight. The yellow precipitate thatformed overnight was filtered. To the filtrate,approximately 13 mL of hexane was added. Orangeprecipitate that formed was filtered and washed with4/1 ethyl ether/hexane mixture and dried. Yield = 32%. Product was characterized by 1H NMR. ( , CDCl3,ppm: 7.3, 7.9, m, 20H, phenyl groups; 4.55, s, 5H,C5H5; 2.5, m, 4H, -CH2-).In order to study the effect of reaction parameterson product yield, reaction parameters such as holdtime, ramp time and temperature was varied. In atypical reaction involving change in hold time,reactions were performed for 5 minutes, 6 minutes, 7minutes and 8 minutes. Temperature was kept constantat 95 oC for all the reactions. Results from thesereactions are shown in Table 1.A second set of reactions was performed byvarying the temperature of the microwave reactor.204Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36Published by Arkansas Academy of Science, 2013Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)Journal of the Arkansas Academy of Science, Vol. 67, 2013205Reactions were performed at 95, 85, 80 and 70 oC. Thehold time was kept constant at 5 minutes. Results fromthese reactions are shown in Table 2. For the last twotrials with a reaction temperature of either 80 or 70 oC,pure product was not obtained; therefore, no yield wasreported.Table 1: Reaction parameters and yields from holdtime trialsHoldtime(min)T( oC)Ramptime(min)Actualyield(g)%yield5 95 10 0.012 306 95 12 0.004 107 95 14 0.006 208 95 16 0.008 20Table 2: Reaction parameters and yields fromtemperature trialsT(oC)Holdtime(min)Ramptime(min)Actualyield(g)%yield95 5 10 0.013 32.85 5 10 0.009 2080 5 10 No yield No yield70 5 10 No yield No yieldThe last set of reactions was performed by varyingthe ramp time. Reactions were performed for 7minutes, 8 minutes, 9 minutes and 10 minutes. Thehold time was kept constant at 5 minutes, and thetemperature was maintained at 95 oC. Results fromthese reactions are shown in Table 3.From the trials performed by varying reactionparameters, the reaction performed for a ramp time of8 minutes and a hold time of 5 minutes at 95 oC gavethe highest yield (38%). Setup time for microwavereactions is 10 minutes, and the reactions take as longas 5-10 minutes for each tube, so overall time for thereaction is 15-20 minutes for each reaction tube. It wasnoticed that yields from multiple reaction tubes rangedfrom a low of 2.5% to a maximum of 37%, whichTable 3: Reaction parameters and yields from ramptime trialsRamptime(min)T( oC)Holdtime(min)Actualyield(g)%yield10 95 5 0.012 309 95 5 0.009 208 95 5 0.015 387 95 5 0.006 20meant that several tubes had to be prepared to get therequired gram amounts necessary for further reactions.By comparison, the set up time for the reaction usingconventional heating is less than 10 minutes, butinvolves a longer reaction time (15-16 hours). Theyield obtained from this reaction (80 %, Ashby et al.1979) is approximately equal to yields obtained from 5microwave reaction tubes combined.Better yields are achieved by conventional heatingcompared to our microwave synthesis. The microwavesynthesis results in a decrease in reaction time. Thus, iftime is a factor, microwave synthesis is a better methodfor synthesizing CpRu(dppe)Cl, whereas if higheryields are required, conventional heating is a bettermethod for synthesizing CpRu(dppe)Cl.In conclusion, microwave-assisted synthesis can beutilized for the preparation of CpRu(dppe)Cl, but thepoor yields and difficulty in purifying the reactionproduct makes the conventional literature preparation(Ashby et al. 1979) the preferred synthetic techniquefor the preparation of CpRu(dppe)Cl.AcknowledgmentsThe authors thank Arkansas State University andthe Department of Chemistry and Physics for theirsupport of this project.Literature CitedAnderson TJ, JR Scott, F Millett and B Durham.2006. Decarboxylation of 2,2’-bipyridinyl-4,4’-dicarboxylic acid diethyl ester during microwavesynthesis of the correspondiong trichelatedruthenium complex. Inorganic Chemistry45:3843-3845.205Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36http://scholarworks.uark.edu/jaas/vol67/iss1/36S. Muthyala and M. DraganjacJournal of the Arkansas Academy of Science, Vol. 67, 2013206Ashby GS, MI Bruce, IB Tomkins and RC Wallis.1979. Cyclopentadienyl-ruthenium and osmiumchemistry. VII. Complexes containing nitriles,tertiary phosphines or phosphites formed byaddition or displacement reactions. AustralianJournal of Chemistry 32:1003-1016.Basato M, A Biffis, G Buscemi, E Callegaro,M Polo, C Tubaro, A Venso, et al. 2007.Reaction of cyclopentadienyl ruthenium complexeswith a carborane anion: effect of the spectatorligands on the substitution site. Organometallics26:4265-4270.Beckford FA, M Shaloski, G Leblanc, J Thessing,LC Lewis-Alleyne, AA Holder, L Li and NPSeeram. 2003. Microwave synthesis of mixedligand diimine-thiosemicarbazone complexes ofruthenium(II): biophysical reactivity andcytotoxicity. Dalton Transactions 2003:10757-10764.Bowie JH, MI Bruce, MA Buntine, AS Gentleman,DC Graham, PJ Low, GF Metha, et al. 2012.Facile decarboxylation of propiolic acid on aruthenium center and related chemistry.Organometallics 31:5262-5273.Bruce MI, K Costuas, F Gendron, J-F Halet,M Jevric and BW Skelton. 2012. Oxidativedimerization of aryldiynyl-ruthenium complexes.Organometallics 31: 6555-6566.de Moura EM, HGL Siebald, GM de Lima,OA Porto, CV Rodarte de Moura and MHorner. 2003. The synthesis and structuralcharacterization of Ru-Sn based derivativesbearing asymmetric X2ClSn- (X= Br and F) anions.Journal of Molecular Structure 658:71-78.di Vaira M, M Peruzzini, SS Costantini andP Stoppioni. 2006. Hydrolytic disproportionationof coordinated white phosphorus in[CpRu(dppe)( 1-P4)]PF6 [dppe = 1,2-bis(diphenylphosphino)-ethane]. Journal ofOrganometallic Chemistry 691:3931-3937.Greene DL and DMP Mingos. 1991. Application ofmicrowave dielectric loss heating effects for therapid and convenient synthesis of ruthenium(II)polypyridine complexes. Transition MetalChemistry 16:71-72.Harvey A, M Draganjac, S Chui, R Snell, andE Benjamin. 2009. Microwave Synthesis of cis-Dichlorotetrakis(dimethylsulfoxide)ruthenium(II).Journal of the Arkansas Academy of Science63:185.Kingston HM and SJ Haswell (eds.). 1997.Microwave-enhanced chemistry: fundamentalssample preparation and application. Washington,DC: American Chemical Society. 772.Matsumura-Inoue T, M Tanabe, T Minami andT Ohashi. 1994. A remarkably rapid synthesis ofruthenium(II) polypyridine complexes bymicrowave irradiation. Chemistry Letters1994:2443-2446.Shaw AP, BL Ryland, JR Norton, D Buccella andA Moscatelli. 2007. Electron exchange involving asulfur-stabilized ruthenium radical cation.Inorganic Chemistry 46:5805-5812.Shawakfeh K, M El-khateeb, D Taher, H Gorls andW Weigand. 2008. Half-sandwich rutheniumcomplexes of pentafluorobenzenethiolato ligands.Transition Metal Chemistry 33:387-391.Sun Y, ML Machala and FN Castellano. 2010.Controlled microwave synthesis of Ru(II) synthonsand chromophores relevant to solar energyconversion. Inorganica Chimica Acta 363:283-287.Treichel PM, MS Schmidt and RA Crane. 1991.Synthesis of new cyclopentadienyliron and -ruthenium benzenethiolate, thiol, and thio ethercomplexes. Inorganic Chemistry 30:379-81.Zagermann J, M Mariusz and N Metzler-Nolte.2011. Microwave-assisted synthesis of the Tpsandwich compound TpRu(p-Br-C6H4Tp) andapplication of its benzoic acid derivative TpRu(p-CO2H-C6H4Tp) in the covalent labeling ofbiomolecules. Dalton Transactions 2011:1011-1015.206Journal of the Arkansas Academy of Science, Vol. 67 [2013], Art. 36Published by Arkansas Academy of Science, 2013

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Microwave Assisted Synthesis of Chloropentahaptocyclopentadienediphenylphosphinoethaneruthenium(II)

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