Author Topic: CTH & Sonochemistry Papers offer - any takers?  (Read 1263 times)

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mellow

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CTH & Sonochemistry Papers offer - any takers?
« on: April 06, 2004, 09:57:00 AM »
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

  • Guest
Most are unknown to the Hive.
« Reply #1 on: April 06, 2004, 11:59:00 AM »
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)



mellow

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More offers: C-alkylations + C-C bond formation
« Reply #2 on: April 08, 2004, 12:40:00 AM »
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

  • Guest
CTH papers wanted!!
« Reply #3 on: April 20, 2004, 07:33:00 AM »
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!


Rhodium

  • Guest
CTH reduction of various functional groups
« Reply #4 on: May 16, 2004, 10:35:00 AM »
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.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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.


Rhodium

  • Guest
CTH Reductions Using Ammonium Formate
« Reply #5 on: June 10, 2004, 04:49:00 PM »
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.thevespiary.org/rhodium/Rhodium/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, ?,?-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.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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