|
Main Index Search Register Login Who's Online FAQ Links | |
||
|
|
|||
|
||||
| 1 Online, 0 Active | You are not logged in | |||
|
|
Novel Discourse | |
|
|
|
|
All 8 posts | Subject: CTH & Sonochemistry Papers offer - any takers? | Please login to post | Down | |
|||
|
|
|
|
|
|||||||||||||||||||||||||||||||
|
mellow (Hive Bee) 04-06-04 16:57 No 499369 |
|
CTH & Sonochemistry Papers offer - any takers? | ||||||||||||||||||||||||||||||
|
Is anyone interested in any of the following? I have them but would need to scan them before posting (most likely in .DjVu format)? CTH * Chem. Rev. 1985, 85, 129-170; R. Johnstone, A. Wilby & I Entwistle; Heterogeneous CTH and Its Relation to Other methods for reduction of Organic Compounds (big review) * TL 25, #32, pp. 3415-8, 1984; S. Ram & R. E. Ehrenkaufer; A General Procedure for Mild and Rapid reduction of aliphatic and aromatic nitro compounds using Amm. Formate as a CTH agent. * TL 29, #31, pp. 3741-4, 1988; S. Ram & L. D. Spicer; Reduction of aldehydes & Ketones to methylene derivs. using Amm Formate as a CTH agent * TL 26, #11, pp. 1381-4, 1985; M. K. Anwer & A. F. Spatola; Applications of Amm. Formate CTH - IV: A facile method for dehalogenation of aromatic chlorocarbons. * TL 29, #45, pp. 5733-4, 1988; A. Barrett & C. Spilling; Transfer hydrogenation: A stereospecific method for the conversion of nitro alkanes into amines. * Tetr. 47, #40, pp. 8587-8600, 1991; B. K. Sarmah & N. C. Barua; Al-NiCl2.6H2O-THF: A new mild and neutral system for selective reduction of organic functional groups. * Synthesis, Feb. 1988, pp. 91-95; S. Ram & R. E. Ehrenkaufer; Amm. Formate in Organic Synthesis: A Versatile Agent in CTH Reductions. * J. Chem. Ed. 71, #11, 1994, pp 992-3; S. De, G Gambhir & H. K. Krishnamurthy; A simple & safe catalytic hydrogenation of 4-Vinylbenzoic acid. [CTH reduction of vinyl to alkane using Pd/C, HCOO.NH4 in MeOH] * J. Chem. Ed. 74, #4, 1997, pp. 430-431; R. W. Hanson; CTH Reactions for Undergrad Practical Programs. Organometallics 1993, 12, 5020-2; E. Gordon, D. Gaba, K. Jebber & D. Zacharias; CTH of Benzaldehyde in a microwave oven. * J. Chem. Soc. Chem. Commun. 1988, 1275-6; A. Banerjee & D. Mukesh; Heterogeneous CTH of 4-Nitrodiphenylamine to p-Phenylenediamines. Sonochemistry * Synthesis Nov. 1989, pp. 787-813; C. Eihorn, J. Einhorn & J-L. Luche; Sonochemistry - The use of ultrasonic waves in synthetic organic chemisty. (big review) * pp. 368-9 from Chapter 8 "Ultrasound as a new tool for synthetic chemists" from the book "Chemistry under extreme or non-classical conditions", Wiley, 1997 (a discussion of catalyst preparation - well worth having). * J. Chem. Ed. 73(s) 1996, A104; F. G. Braga; Inexpensive Small-scale sonochemistry with magnetic agitation. * Ultrasoncis Sonochemistry 1994, 1, #1, S45-6; P. Cains, L. McCausland, D. Bates & T. Mason; Sonochemical hydrogenation over metal catalysts. * TL 40 (1999), 7855-6; D. Nagaraja & M. Pasha; Reduction of Aryl nitro compounds with Al/NH4Cl: Effect of Ultrasound on the Rate of Reation. * J. Chem. Ed. 63, #5, May 1986, pp. 427-9; P. Boudjouk; Synthesis with Ultrasonic Waves. (an introduction) I can't possibly guess what files Rhodium is hosting as PDFs (I hope he knows!). I'll only be prepared to rush these for ya if you are willing to host them so that others may look at them. People who just want them for their private collections may have to wait. |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
Rhodium (Chief Bee) 04-06-04 18:59 No 499387 
|
|
Most are unknown to the Hive. | ||||||||||||||||||||||||||||||
|
I can't possibly guess what files Rhodium is hosting as PDFs (I hope he knows!). Most of the PDF files at my page has been linked from various posts here at the Hive, so just UTFSE for volume/starting page/year if you want to see if a specific article has been posted. Of the CTH references, only two has been posted here before: #1: Post 455063 (Rhodium: "The Discovery of Catalytic Transfer Hydrogenation", Tryptamine Chemistry) #5: Post 435002 (Aurelius: "Transfer Hydrog. Nitro to amine keep configuration", Methods Discourse) The Hive - Clandestine Chemists Without Borders |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
mellow (Hive Bee) 04-07-04 10:06 No 499496 |
|
Sonochem hydrogenation of metal catalyst (Rated as: excellent) |
||||||||||||||||||||||||||||||
|
Here's a paper worth reading. look at the results for Pd/C and think about making an instant Nickel catalyst out of nothing but precipitated Nickel and ultrasound. Ultrasonics Sonochemistry 1994 Vol 1 No 1 S45 - S46 Sonochemical hydrogenation over metal catalysts P.W. Cains, L.J. McCausland, D.M. Bates* and T.J. Mason* AEA Technology, Harwell Laboratory, Didcot, Oxon OX11 ORA, UK * Coventry University, Priory Street, Coventry CV1 5FB, UK Abstract: Ultrasound has been used to activate 3 µm Ni powder as a hydrogenation catalyst to give 65% conversion of oct-1-ene to octane. The effect on submicrometre Ni powders was less marked, and the activity of Raney Ni was reduced. Insonation of a Pd/C catalyst increased both the adsorptive uptake of hydrogen and hydrogenation rates. Keywords: hydrogenation; nickel catalyst; morphology The irradiation of various catalytic powders with power ultrasound causes remarkable changes in their character vis-a-vis aggregation, particle morphology and thickness of the surface oxide coating. Sometimes, but by no means always, this is reflected in their catalytic activity. Boudjouk et al.1 report the application of ultrasound to the hydrosilylation of styrene over a Pt/C catalyst yielding 95% over 2h at room temperature and pressure, compared to the 'silent' reaction requiring temperatures above 100 °C and pressures over 5 bar. Selective hydro- genations of alkenes over Pt/C at room temperatures and pressures using donor compounds such as formic acid and hydrazine have also been reported2,3. Simple nickel powder is an extremely inactive catalyst for the hydro- genation of alkenes, however, high intensity ultrasound has been used to activate nickel powder for use as a hydrogenation catalyst4. Surface studies of the metal after sonication reveal dramatic changes in morphology in that the surfaces are smoothed and, as the individual particle size is reduced the particles begin to come together and form extended aggregates4. We have addressed ourselves to the question of the effect of ultrasound on the catalytic activity of different types of nickel catalyst (3 µm, submicrometre, Raney) and 10% palladium on carbon. The model system chosen was the hydrogenation of oct-1-ene to octane [Equation (1)] employing methodology similar to that of Suslick5 using a Sonic Systems6 20 kHz probe system. C6H13-CH=CH2 __> C6H13-CH2-CH3 {Conditions: H2 / Cat} . . . (1) The reduction of 1-octene to octane over ultrasonically treated Ni powders Hydrogenation with 3 µm nickel powder We have investigated the hydrogenation of 1-octene with gaseous hydrogen in the presence of 3 µm Ni powder (Aldrich) over a range of insonation, mixing and temperature conditions. Experiments have been carried out using a 3.5 mm insonation probe with 0.085 mol 1-octene, 5 g Ni powder in 250 ml ethanol solvent with a hydrogen sparge of 0.4 mol h-1. The insonation of the catalyst suspension under a nitrogen atmosphere was carried out before it was used for hydrogenation under mechanical stirring at ca 100 rpm. Optimum catalytic activity was obtained with 3 µm Ni pre-sonicated for 1 h at 10 °C using 34 W total power. Under these conditions 65% octane was obtained after 60 min hydrogenation at 25 °C compared with no octane using untreated catalyst (Table 1). The increase in activity induced by ultrasound can be explained by a combination of factors such as the removal of impurities from the surface of the nickel, a reduction in the thickness of the oxide coating, activation of the surface and reduction in the particle size of the material thereby increasing the surface area of the catalyst available for reaction. No hydrogenation occurred (a) when the insonation power was reduced to below the cavitation threshold or was omitted entirely, (b) when no stirring was provided during hydrogenation, (c) when insonation and hydro- genation were carried out simultaneously, or (d) at hydrogenation temperatures above 60 °C. Substitution of a magnetic stirrer for a mechanical stirrer during hydrogenation caused magnetization of the pre-sonicated catalyst particles and a reduction in yield from 65 to 40%. We have also confirmed an observation by Suslick5 that there is an optimum in catalytic activity at an insonation time of 1 h, under our conditions the activity reduced to almost zero after 2 h sonication. Table 1. Hydrogenation of oct-1-ene*
* 20 kHz, 34 W, 25 °C, absolute ethanol Hydrogenation with submicrometre nickel powder As with 3 µm nickel the untreated powder proved to be an ineffective catalyst and sonication was carried out using the optimum conditions developed above. In this case however the effect of sonication was significantly smaller with only 15% octane produced in the same time using the activated material (Table 1). This is somewhat contrary to what might be expected, but optical micrographs indicate that the submicrometre catalyst forms large agglomerates on insonation which may have less activity. Hydrogenation with Raney nickel In complete contrast to the results above insonation of Raney nickel produced a reduction in catalytic efficiency (Table 1). The as-supplied material (Type 2, Aldrich) gave 100% conversion after 30 min under conventional conditions compared to only 25% conversion after 30 min after insonation. A gas-liquid chromatography (GLC) study of the reaction products during hydrogenation suggested that the insonated catalyst promoted iso- merization at the expense of hydrogenation. Thus after 30 min hydrogenation using untreated Raney nickel there was 100% octane, 0% oct-2-ene whereas in contrast, the use of pre-insonated Raney nickel gave 37% octane, 20% oct-2-ene and 6% unreacted oct-1-ene after 1 h. Due to its method of preparation Raney nickel has a high surface area and considerable porosity. It seems reasonable to conclude that Raney nickel which has been irradiated with ultrasound may agglomerate and consolidate, therefore reducing its catalytic activity. Raney Nickel is also free of the passivating layers found on the other nickel powders studied and so it would not be expected that sonication would affect its activity in the same way as the other two nickel powders. Hydrogenation with 10% Pd on carbon Pre-sonication of this catalyst achieved a considerable enhancement in activity resulting in 100% conversion after only 30 min for the sonicated system (Table 1). For the as-supplied 10% Pd/C only 66% conversion was achieved after 30 min. This enhancement in activity appeared to correlate with an adsorptive uptake of hydrogen on the catalyst of 10 ml (STP)g-1 (0.45 mmol g-1) without insonation to 40 ml g-1 (1.78 mmol g-1) at an intensity of 160 W cm-2. Conclusion Sonicated 3 µm nickel powder was found to be a more efficient catalyst than similarly treated submicrometre nickel powder although both materials were inactive without ultrasonic activation. Raney Nickel decreased in catalytic activity for the hydrogenation of oct-1-ene after ultrasonic pre-treatment. Pre-irradiated palladium-on- carbon was found to be the most effective catalyst for the conversion of oct-1-ene to octane. There appears to be an obvious advantage in using a pre-sonicated palladium catalyst in terms of the rate of oct-1-ene hydrogenation. However, in terms of cost efficiency, using this catalyst in a hydrogenation reaction is very expensive compared to 3 µm nickel. Acknowledgement We thank SERC for a case award (D.M.B.). References 1. Han, B.H. and Boudjouk, P. Organometallics (1983) 2 770 2. Boudjouk, P. and Han, B. H. J Catalysis (1983) 79 489 3. Shin, D.H. and Han, D.H. Bull Korean Chem Soc (1985) 6 247 4. Suslick, K.S., Casadonte, D.J. and Doktycz, S.J. Solid State Ionics (1989) 32/33 444 5. Suslick, K.S. Practical Sonochemistry (Ed. Mason, T.J.) Ellis Horwood, New York, USA (1991) 164 6. Sonic Systems, Monks Dairy, Isle Brewers, Taunton, Somerset TA3 6QL, UK |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
mellow (Hive Bee) 04-08-04 07:40 No 499678 |
|
More offers: C-alkylations + C-C bond formation | ||||||||||||||||||||||||||||||
|
C-alkylations and C-C bond formation. via alkyl halide, PTC & Schiff base deriv. of monoalkyl amino acids. Summary (of (1) to (10): C-alkylation of (Subst.) Benzyl halide via an amino acid (such as alanine or glycine, etc.). to give the corresponding benzyl-alanine, benzyl-glycine, which can, subsequently be decarboxylated to give a phenethylamine. (analogous reactions could also work to give tryptamines). 1) Sterically Controlled Synth of alpha-methyldopa, Chem. & Ind. 1972, 687-688. Synthesis of amino acids. 2) The Synth. of amino acids by PTC. (O'Donnell & Co). TL 30 (1978), 2641-2644. 3) Alkylation of aldimine and ketimine derivs. of glycine ethyl ester under PTC.; TL 23, #41 (1982), 4255-4258. Martin O'Donnell & Co. 4) alpha-amino acids by PTC.; TL 23, #41 (1982), 4259-4262. Martin O'Donnell & Co. Abstract: alpha-amino acids, alpha-methyl p-chlorophenylalanine, alpha-methyl p-tyrosine, alpha-methyl m-tyrosine and alpha-methyl DOPA have been prepared in good yields from amino ester hydrochlorides. The key step is the PTC alkylation of Schiff base deriv. of monoalkyl amino acids. 5) alpha-alkylation of amino acids without racemization. Prepn. of either (S)- or (R)- alpha-methyl DOPA from (S)-alanine. Helv. Chim. Acta 68 (1985), 144-154. 6) Amino acids & Peptides. XXVIII. A New Synth. of alpha-amino acid derivs. by alkylation of Schiff bases derived from Glycine & Alanine. Chem. Pharm. Bull. 25(9) 2287-2291 (1977). 7) Liebigs Ann. Chem. 1981, 696-708 (German); Asymmetrische Synthese von alpha-Methylaminosauren durch Alkylieren des lithiierten Lactimethers van cyclo-(L-Ala-L-Ala) 8) The Synth. of amino acid derivs. by PTC alkylations. TL 47 (1978), 4625-4628. 9) Alkylation of protected alpha-amino acid derivs. in the presence of Pot. Carb. Synthesis April 1984, 313-315. 10) Microwave irradiated Alkylations of Active methylenes under solid-liquid PTC conditions. Y Jiang, Y Wang, R Deng & A Mi; From Phase-Transer Catalysis (Chapter 16), Ed. Marc Halpern, ISBN: 0841234914. Darzens & variants. 11) Reactions of Organic anions. XLIII. Catalytic method for synth. of Glycidic nitriles in aq. medium. TL 23 (1972), 2395-2396. 12) Stereochemical control of interfacial Darzens Condensation. JCS Chem. Comm. 1977, 902-903. 13) Two Phase Darzens Condensation Rxn with Octopus Cpds as a Catalyst. Bull. Chem. Soc. Jpn. 53 (1980), 1463-1464. Whatever 14) beta-2,5-dihydroxyphenyl-DL-alanine. Biochemical Preparations 3 (1953). 79-83. |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
armageddon (Newbee) 04-20-04 14:33 No 501805 
|
|
CTH papers wanted!! | ||||||||||||||||||||||||||||||
|
Hi mellow! I'm very interested in the following articles, as my understanding of CTHs isn't as good as I would like it to be...  I really would bee very happy if u could scan, upload and link them (besides, some of them are cited in old CTH docs on rhodiums page and would give a nice additional link inside these documents  )Tetrahedron 25, #32, pp. 3415-8, 1984; S. Ram & R. E. Ehrenkaufer; A General Procedure for Mild and Rapid reduction of aliphatic and aromatic nitro compounds using Amm. Formate as a CTH agent. Tetrahedron 26, #11, pp. 1381-4, 1985; M. K. Anwer & A. F. Spatola; Applications of Amm. Formate CTH - IV: A facile method for dehalogenation of aromatic chlorocarbons. Synthesis, Feb. 1988, pp. 91-95; S. Ram & R. E. Ehrenkaufer; Amm. Formate in Organic Synthesis: A Versatile Agent in CTH Reductions. J. Chem. Ed. 74, #4, 1997, pp. 430-431; R. W. Hanson; CTH Reactions for Undergrad Practical Programs. Thanks! "..ein Trank von unterschiedlicher Farbe, in ihm ist Heilung für die Menschen." |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
Rhodium (Chief Bee) 05-16-04 17:35 No 507520
|
|
CTH reduction of various functional groups (Rated as: excellent) |
||||||||||||||||||||||||||||||
|
Reduction of Aldehydes and Ketones to Methylene Derivatives Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent Siya Ram and Leonard D. Spicer Tetrahedron Letters 29(31), 3741-3744 (1988) (https://www.rhodium.ws/chemistry/cth.carbonyl.deoxygenation.html) Summary Various aromatic aldehydes and ketones were reduced to the corresponding hydrocarbons using ammonium formate as the hydrogen source. ____ ___ __ _ A General Procedure for Mild and Rapid Reduction of Aliphatic and Aromatic Nitro Compounds Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent Siya Ram and Richard F. Ehrenkaufer Tetrahedron Letters 25(32), 3415-3418 (1984) (https://www.rhodium.ws/pdf/nitro.cth-formate.pdf) Abstract Various aliphatic and aromatic nitro compounds were selectively and rapidly reduced to their corresponding amino derivatives in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent. ____ ___ __ _ Catalytic Transfer Hydogenation Reactions for Undergraduate Practical Programs R. W. Hanson J. Chem. Educ. 74, 430 (1997) (https://www.rhodium.ws/pdf/cth.reactions-j.chem.ed.pdf) Abstract A brief review of catalytic transfer hydrogenation (CTH) reactions is given. Attention is drawn, particularly, to the utility of ammonium formate as the hydrogen donor in this type of reaction. The reduction of aryl carbonyl compounds to the corresponding methylene derivatives by ammonium formate in the presence of 10% Pd/C at 110°C is compared to their reductive ammonation which occurs at higher temperatures in the absence of the catalyst (the Leuckart reaction). It is suggested that the low cost and simplicity of CTH reactions using ammonium formate as the hydrogen donor, together with the high yields obtained in many cases, make them excellent candidates for inclusion in undergraduate practical programmes. Laboratory instructions are given for the reduction of nitrobenzene to aniline (isolated as benzanilide), benzophenone to diphenylmethanol and fluorenone to fluorene, in all cases using ammonium formate as the hydrogen donor and 10% Pd/C as the catalyst. Thin layer chromatography shows that in each case the product is homogeneous; the yields are essentially quantitative. The Hive - Clandestine Chemists Without Borders |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
Rhodium (Chief Bee) 06-10-04 23:49 No 512653
|
|
CTH Reductions Using Ammonium Formate (Rated as: excellent) |
||||||||||||||||||||||||||||||
|
Catalytic Hydrogen Transfer Reductions Using Ammonium Formate - A Review Brindaban C. Ranu, Arunkanti Sakkar, Sankar K. G. and K. Ghosh J. Indian Chem. Soc. 75, 690-694 (1998) (https://www.rhodium.ws/chemistry/cth.af.review.html) Abstract An account of recent developments on selective reduction of several important functional groups by catalytic transfer hydrogenation using ammonium formate and palladium or nickel is presented. This includes reduction of nitro alcohols, α,β-unsaturated nitroalkenes, quinoline and isoquinoline, carbonyl functionalities, carbon-carbon double bond in conjugation to carbonyl, sulfonyl and phosphonate moieties, and epoxides. Deoxygenation of heteroaromatic N-oxides and deprotection of 1,3-dibenzyluracils have also been addressed. ____ ___ __ _ Transfer Hydrogenation: Stereospecific Reduction of Nitroalkanes to Amines Anthony G. M. Barrett and Christopher D. Spilling Tetrahedron Letters 29(45), 5733-5734, (1988) (https://www.rhodium.ws/chemistry/nitro2amine.cth.pd-af.html) Abstract A series of nitroalkanes were converted into the corresponding amines with retention of configuration by transfer hydrogenation using ammonium formate and Pd/C. This article has been posted before in Post 435002 (Aurelius: "Transfer Hydrog. Nitro to amine keep configuration", Methods Discourse) ____ ___ __ _ Ammonium Formate in Organic Synthesis: A Versatile Agent in Catalytic Hydrogen Transfer Reductions Siya Ram, Richard E. Ehrenkaufer Synthesis 91-95 (1988) (https://www.rhodium.ws/pdf/ammonium.formate.cth.review.pdf) Applications of ammonium formate in organic synthesis are reviewed. 1. Introduction 2. Reduction of Functional Groups  2.1. Initial Studies 2.2. Azides 2.3. Nitro Groups 2.4. Nitriles 3. Dehalogenation of Aromatic Chlorocarbons 4. Deprotection of Functional Groups 4.1. Deprotection of Polymer and Carbobenzyloxy Group from Protected Peptides 4.2. Deprotection of O-Benzyl Group 5. Regioselective Synthesis of 1-Olefins 6. Miscellaneous Applications and Other Formic Acid Derivatives 7. Conclusion The Hive - Clandestine Chemists Without Borders |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||
|
|
|
|||||||||||||||||||||||||||||||
|
Rhodium (Chief Bee) 09-29-04 16:41 No 533763
|
|
CTH Reduction of Ketones to Hydrocarbons (Rated as: excellent) |
||||||||||||||||||||||||||||||
|
A Simple Reduction of Aralkyl Ketones to Alcohols A. S. Radhakrishna, K. R. K. Prasad Rao, S. C. Nigam, R. Bakthavatchalam and B. B. Singh Org. Prep. Proced. Int. 21(3), 373-375 (1989) Catalytic transfer hydrogenation has been widely studied in the past three decades.1 Palladium-catalysed ammonium formate reduction of aromatic halides,2 nitriles,3 nitro compounds2,4 and α,β-unsaturated carbonyl compounds5 has been reported. Aromatic ketones are reduced to the corresponding aromatic hydrocarbons using Pd/C-formic acid in refluxing ethanol;6 aromatic aldehydes and ketones are also reduced to the hydrocarbons using palladium-carbon/cyclohexene or limonene.7 The hitherto undescribed reduction of aralkyl ketones to alcohols using palladium-carbon-ammonium formate is now reported to proceed in high yields at room temperature. The completion of reductions was followed by TLC. Aromatic aldehydes failed to give the alcohols under the same conditions. Experimental Section General Procedure To a stirred suspension of an appropriate ketone (20 mmol) and 10% Pd/C (1.5-1.6 g) in dry methanol (25 ml), anhydrous ammonium formate was added (50 mmol) in a single portion. The resulting reaction mixture (slight exotherm and effervescence) was stirred at room temperature for 4 hrs. under N2. The catalyst was then removed by filtration through Celite and washed with methanol (20 ml). The filtrate was evaporated under reduced pressure. The resulting residue was diluted with water (50 ml) and the product extracted with chloroform and the solution was dried over Na2SO4. Distillation of the solvent gave the pure alcohol. Table Reduction of Aralkyl Ketones to Alcoholsd
a) Products were characterised by comparison (IR, 1H-NMR, TLC and bp.) with authentic samples prepared by reduction of ketones with sodium borohydride. Isolated yields are based on a single experiment and are not optimized. All reactions were carried out for 4 h. b) Dictionary of Organic Compounds, 4, 2687; c) L. Zechmeirter and S. Rom., Ann., 468, 117 (1929); d) A. M. Kuliev et. al., Azerb. Khim. Zh., 85 (1966); C. A., 65, 1359b (1967). References [1] R. A. W. Johnstone, A. H. Wilby, I. D. Entwistle, Chem. Rev., 85, 129 (1985) Post 455063 (Rhodium: "The Discovery of Catalytic Transfer Hydrogenation", Tryptamine Chemistry) [2] N. A. Cortese and R. F. Heck, J. Org. Chem., 42, 3491 (1977) [3] G. R. Brown and A. J. Foubister, Synthesis, 1036 (1982) [4] J. R. Weir and R. F. Heck, J. Org. Chem., 45, 4992 (1980) [5] N. A. Cortese and R. F. Heck, J. Org. Chem., 43, 3985 (1978) [6] Hsu Ching Shih, et al., Hua Hsueh 43, 142 (1985) [7] G. Brieger and T. H. Fu., J. Chem. Soc. Chem. Commun 757 (1976) [See below] Catalytic Transfer Reduction of Carbonyl Compounds Gottfried Brieger and Tzuu-Heng Fu J.C.S. Chem. Comm. 757 (1976) (https://www.rhodium.ws/pdf/cth.deoxygenation.pdf) Summary Aromatic aldehydes and ketones can be reduced to the corresponding hydrocarbons in good yield by catalytic transfer reduction using cyclohexene or limonene as donor, palladium-carbon as catalyst, and a Lewis acid promotor such as ferric chloride. The Hive - Clandestine Chemists Without Borders |
||||||||||||||||||||||||||||||||
|
|
|||||||||||||||||||||||||||||||