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All 11 posts Subject: Oximes from Nitroalkenes using Decaborane CTH Please login to post Down

Rhodium
(Chief Bee)
09-11-03 21:23
No 458467
User Picture       Oximes from Nitroalkenes using Decaborane CTH
(Rated as: excellent)

Catalytic transfer hydrogenation of conjugated nitroalkenes using decaborane: synthesis of oximes
By S. H. Lee, Y. J. Park and C. M. Yoon
Org. Biomol. Chem. 1(7), 1099-1100 (2003) (https://www.rhodium.ws/chemistry/cth.nitroalkene2oxime.html)

Abstract

α,β-Unsaturated nitroalkenes are readily reduced to the corresponding aldoximes and ketoximes in good yields, using a system of decaborane (B₁₀H₁₄) and DMSO in methanol in the presence of 10% Pd/C at room temperature under nitrogen.

Rhodium
(Chief Bee)
05-27-04 01:18
No 509830
User Picture       Hypophosphite CTH: Nitroalkenes to Oximes
(Rated as: good read)

Palladium-Sodium Hypophosphite CTH: Reduction of Nitroalkenes to Oximes
Rajender S. Varma, Manju Varma and George W. Kabalka
Synthetic Communications 16(1), 91-96 (1986) (https://www.rhodium.ws/chemistry/cth.ns2oxime.pd-na-hypo.html)

Abstract
α,β-Unsaturated nitroalkenes are readily reduced by sodium hypophosphite to the corresponding oximes in the presence of palladium.

^{The Hive - Clandestine Chemists Without Borders}

Aurelius
(Active Asperger Archivist)
05-27-04 02:28
No 509846
      To bees with access to literature

I think a digest on Kabalka's works would be wonderful. I know that Rhodium has access to most of his works, but it would be great if somebody else would create (at least the beginnings) a digest of his papers.

I would do this myself, but I don't have readily accessible literature materials right now. And it may be a few months before I do again.

Thanks to the bees for considering this request!

tongue

Act quickly or not at all.

Rhodium
(Chief Bee)
05-27-04 05:23
No 509869
User Picture       Varma vs. Kabalka

I think a digest on Kabalka's works would be wonderful.

Not to say impossible... He's an extremely prolific author, publishing 230+ papers only between 1990-2002: http://atom.chem.utk.edu/kabalka/pubs.html

Unfortunately a lot of his writings are rather dull, the best stuff he's done has nearly always been co-authored with Rajender S. Varma, so I believe that any digest should be on the topic of Varma's works instead. I have not found a full bibliography of his works as of yet.

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
05-28-04 02:48
No 509994
User Picture       Varma & Kabalka: Nitroalkene Reduction Review
(Rated as: excellent)

Selected Reductions of Conjugated Nitroalkenes
George W. Kabalka, Laila H. M. Guindi and Rajender S. Varma
Tetrahedron 46(21), 7443-7457 (1990) (https://www.rhodium.ws/chemistry/nitrostyrene.reduction.review.html)

Abstract
Conjugated nitroalkenes are readily reduces by a variety of borane and borohydride reagents.
The reactions provide a convenient access to a number of nitrogen and oxygen basad functional groups.

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
05-30-04 17:54
No 510333
User Picture       Nitroalkene Synthesis & Reduction Review
(Rated as: excellent)

Syntheses and Selected Reductions of Conjugated Nitroalkenes - A Review
George W. Kabalka & Rajender S. Varma
Org. Prep. Proced. Int. 19(4-5), 283-328 (1987) (https://www.rhodium.ws/chemistry/nitroalkene.synthesis-reduction.review.html)

Table of Contents
I. Introduction
II. Preparation of Conjugated Nitroalkenes
A. From Carbonyl Compounds
B. From Alkenes
C. Miscellaneous Methods
III. Reduction of Conjugated Nitroalkenes
A. Preparation of Nitroalkanes
B. Preparation of Oximes
C. Preparation of Carbonyl Compounds
D. Preparation of N-Substituted Hydroxylamines and Amines
References

I know that the layout sux somewhat, but it's really hard to place so many pictures of different sizes throughout a text without something strange happening in either Mozilla or IE...

Also, could you help me out with the reference link table? I know that at least half of the 150+ referenced articles are available on my site somewhere or here at the Hive, but not exactly where... If you can tell me which reference is found where, I'll add hyperlinks to them from within the review.)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
06-08-04 00:46
No 512099
User Picture       Varma&Kabalka: Cr(II) Nitrostyrene Reduction
(Rated as: excellent)

Chromium(II) Chloride Reduction of Nitrostyrenes: A Facile Route to Oximes
Rajender S. Varma, Manju Varma and George W. Kabalka
Synthetic Communications 15(14), 1325-1332 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2oxime.crcl2.html)

Abstract
α,β-Unsaturated nitroalkenes are rapidly reduced by chromium(II) chloride to oximes.
____ ___ __ _

Chromium(II) Chloride Reduction of Nitroalkenes: A Facile Route to Carbonyl Compounds
Rajender S. Varma, Manju Varma and George W. Kabalka
Tetrahedron Letters 26(32), 3777-3778 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2ketone.crcl2.html)

Abstract
α,β-Unsaturated nitroalkenes are readily reduced by chromium(II) chloride to the corresponding carbonyl compounds in good yields.

_{This article has been posted before in Post 244992 (foxy2: "Chromium(II)Chloride Reduction of Nitroalkenes", Chemistry Discourse)}

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
06-11-04 10:30
No 512771
User Picture       Nitroalkene Reactions
(Rated as: good read)

Conjugated nitroalkenes: versatile intermediates in organic synthesis
Anthony G. M. Barrett, Gregory G. Graboski
Chem. Rev. 86, 751-762 (1986) (https://www.rhodium.ws/pdf/conjugated.nitroalkenes.review.pdf)
____ ___ __ _

_{Reactions of Sodium Borohydride in Acidic Media. V.}
Reduction and Alkylation of Oximes with Carboxylic Acids; A New Synthesis of N,N-Dialkylhydroxylamines
Gribble, Gordon W.; Leiby, Robert W.; Sheehan, Myles N.
Synthesis 856-859 (1977) (https://www.rhodium.ws/pdf/oxime2hydroxylamine.nabh4-rcooh.pdf)
____ ___ __ _

Reduction of nitroalkenes to nitroalkanes with aqueous sodium borohydride
Albert I. Meyers, J. C. Sircar
J. Org. Chem. 32, 4134-4136 (1967) (https://www.rhodium.ws/pdf/nitroalkenes.aq-nabh4.pdf)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
09-03-04 16:51
No 529378
User Picture       CdCl2–Mg–H2O: Nitroalkenes to Keto-compounds
(Rated as: good read)

Cadmium Chloride–Magnesium–Water: A New System for Regioselective Transformation of Conjugated Nitroalkenes to Ketocompounds
Manobjyoti Bordoloi
J. Chem. Soc. Chem. Commun. 922-923 (1993) (https://www.rhodium.ws/chemistry/nitroalkene2ketone.mg-cdcl2.html)

Abstract
Reaction of 6-nitro-Δ5-steroids and nitroalkenes in tetrahydrofuran with CdCl₂–Mg–H₂O furnished 6-ketosteroids and ketocompounds, respectively, in good yield.

^{The Hive - Clandestine Chemists Without Borders}

java
(Hive Addict)
09-05-04 22:25
No 529755
User Picture       Some of R.S.Varma's recent work's........

R.S. Varma, Green Chem. 1, 43-55 (1999)
R.S. Varma, J. Heterocyclic Chem. 35, 1565-1571 (1999)
R.S. Varma, Pure Appl. Chem. 73, 193-198 (2001)
R.S. Varma, Tetrahedron Report # 598, Tetrahedron 58, 1235-55 (2002)
U. Pillai, E. Sahle-Demessie and R.S. Varma, J. Mat. Chem. 12, 3199 (2002)
R.S. Varma, in Microwaves in Organic Synthesis (A. Loupy, Ed.), Chapter 6, pp 181-218, Wiley-VCH, Weinheim (2002).
R.S. Varma, Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation AstraZeneca Research Foundation India, Bangalore, India (2002)
^{(Free copy available on request from: azrefi@astrazeneca.com)}
R.S. Varma, In: Ionic Liquids as Green Solvents. Progress and Prospects, R. Rogers and K. R. Seddon (Eds.), ACS Symposium Series 856, American Chemical Society, Washington, D. C., Chapter 7, pp 82-92 (2003).
R.S. Varma, Microwave Technology-Chemical Applications: Kirk-Othmer Encyclopedia of Chemical Technology, 5th Ed (2004).
Y. Ju and R.S. Varma, Green Chem. 6, 219 (2004)

It is better to die on your feet than to live on your knees.......
-Emiliano Zapata-

indole_amine
(Hive Bee)
09-30-04 04:02
No 533836
User Picture       Reactions promoted by Microwaves and Clays
(Rated as: excellent)

Clay and clay-supported reagents in organic synthesis
Rajender S. Varma
Tetrahedron 58 (2002) p.1235-1255

An overview over the possibilities and applications of different clays in organic chemistry. Solventfree reductive aminations of carbonyl compounds on clay, oxidations of alcohols to carbonyls by clayfen, conversions of aldehydes to nitriles, synthesis of imines and enamines, Friedel-Crafts, Diels-Alder, Suzuki and Heck arylation reactions can be done using clay reagents, as well as dehydrations, isomerizations and addition reactions...

Selective Nitration of Styrenes with Clayfen and Clayan: A Solvent-free Synthesis of β-Nitrostyrenes
Varma, Rajender S.; Naicker, Kannan P.; Liesen, Per J.
Tetrahedron Letters 39, 23 (1998) pp. 3977-3980

Abstract
A facile, solvent-free synthesis of beta-nitrostyrenes is described from styrene and its substituted derivatives using inexpensive "doped" clay reagents, clayfen and clayan.

Looks useful for arriving at ketones in connection with Post 458467 (Rhodium: "Oximes from Nitroalkenes using Decaborane CTH", Novel Discourse)

Solid State Regeneration of Ketones from Oximes on Wet Silica Supported Sodium Periodate Using Microwaves
Varma, Rajender S.; Dahiya, Rajender; Saini, Rajesh K.
Tetrahedron Letters 38, 51 (1997) pp. 8819-8820

Abstract
Microwave irradiation of ketoximes on wet silica supported sodium periodate under solvent-free conditions provides a fast, efficient and simple method for regeneration of ketones.

Clay catalyzed synthesis of imines and enamines under solvent-free conditions using microwave irradiation
(Varma, Rajender S.; Dahiya, Rajender; Kumar, Sudhir)
Tetrahedron Letters 38, 12 (1997) pp. 2039-2042

Abstract
The reactions of primary and secondary amines with aldehydes and ketones, respectively, are accelereated by microwaves under solvent-free conditions in the presence of montmorillonite K 10 clay to afford a high yield synthesis of imines and enamines.

Microwave-assisted oxidation of alcohols under solvent-free conditions using clayfen
(Varma, Rajender S.; Dahiya, Rajender)
Tetrahedron Letters 38, 12 (1997) pp. 2043-2044

Abstract
Adsorbed on clayfen, alcohols are readily oxidized to carbonyl compounds upon exposure to microwaves under solvent-free conditions. Tis rapid, selective and environmentally benign method conserves the use of excess solvents and toxic antioxidants usually employed.

And this transformation can also be undone... smile

Microwave-Assisted Reduction of Carbonyl Compounds in Solid State Using Sodium Borohydride Supported on Alumina
(Varma, Rajender S.; Saini, Rajesh K.)
Tetrahedron Letters 38, 25 (1997) pp. 4337-4338

Abstract
A manipulatively simple and rapid method for the reduction of carbonyl compounds is described that is conducted under solventless "dry" conditions using NaBH₄/alumina and microwave irradiation.

	https://the-hive.archive.erowid.org	the-hive@erowid.org



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	All 11 posts		Subject: Oximes from Nitroalkenes using Decaborane CTH		Please login to post		Down


		Rhodium (Chief Bee) 09-11-03 21:23 No 458467				Oximes from Nitroalkenes using Decaborane CTH (Rated as: excellent)
						Catalytic transfer hydrogenation of conjugated nitroalkenes using decaborane: synthesis of oximes By S. H. Lee, Y. J. Park and C. M. Yoon Org. Biomol. Chem. 1(7), 1099-1100 (2003) (https://www.rhodium.ws/chemistry/cth.nitroalkene2oxime.html) Abstract α,β-Unsaturated nitroalkenes are readily reduced to the corresponding aldoximes and ketoximes in good yields, using a system of decaborane (B₁₀H₁₄) and DMSO in methanol in the presence of 10% Pd/C at room temperature under nitrogen.



		Rhodium (Chief Bee) 05-27-04 01:18 No 509830				Hypophosphite CTH: Nitroalkenes to Oximes (Rated as: good read)
						Palladium-Sodium Hypophosphite CTH: Reduction of Nitroalkenes to Oximes Rajender S. Varma, Manju Varma and George W. Kabalka Synthetic Communications 16(1), 91-96 (1986) (https://www.rhodium.ws/chemistry/cth.ns2oxime.pd-na-hypo.html) Abstract α,β-Unsaturated nitroalkenes are readily reduced by sodium hypophosphite to the corresponding oximes in the presence of palladium. ^{The Hive - Clandestine Chemists Without Borders}



		Aurelius (Active Asperger Archivist) 05-27-04 02:28 No 509846				To bees with access to literature
						I think a digest on Kabalka's works would be wonderful. I know that Rhodium has access to most of his works, but it would be great if somebody else would create (at least the beginnings) a digest of his papers. I would do this myself, but I don't have readily accessible literature materials right now. And it may be a few months before I do again. Thanks to the bees for considering this request! Act quickly or not at all.



		Rhodium (Chief Bee) 05-27-04 05:23 No 509869				Varma vs. Kabalka
						I think a digest on Kabalka's works would be wonderful. Not to say impossible... He's an extremely prolific author, publishing 230+ papers only between 1990-2002: http://atom.chem.utk.edu/kabalka/pubs.html Unfortunately a lot of his writings are rather dull, the best stuff he's done has nearly always been co-authored with Rajender S. Varma, so I believe that any digest should be on the topic of Varma's works instead. I have not found a full bibliography of his works as of yet. ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 05-28-04 02:48 No 509994				Varma & Kabalka: Nitroalkene Reduction Review (Rated as: excellent)
						Selected Reductions of Conjugated Nitroalkenes George W. Kabalka, Laila H. M. Guindi and Rajender S. Varma Tetrahedron 46(21), 7443-7457 (1990) (https://www.rhodium.ws/chemistry/nitrostyrene.reduction.review.html) Abstract Conjugated nitroalkenes are readily reduces by a variety of borane and borohydride reagents. The reactions provide a convenient access to a number of nitrogen and oxygen basad functional groups. ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 05-30-04 17:54 No 510333				Nitroalkene Synthesis & Reduction Review (Rated as: excellent)
						Syntheses and Selected Reductions of Conjugated Nitroalkenes - A Review George W. Kabalka & Rajender S. Varma Org. Prep. Proced. Int. 19(4-5), 283-328 (1987) (https://www.rhodium.ws/chemistry/nitroalkene.synthesis-reduction.review.html) Table of Contents I. Introduction II. Preparation of Conjugated Nitroalkenes A. From Carbonyl Compounds B. From Alkenes C. Miscellaneous Methods III. Reduction of Conjugated Nitroalkenes A. Preparation of Nitroalkanes B. Preparation of Oximes C. Preparation of Carbonyl Compounds D. Preparation of N-Substituted Hydroxylamines and Amines References I know that the layout sux somewhat, but it's really hard to place so many pictures of different sizes throughout a text without something strange happening in either Mozilla or IE... Also, could you help me out with the reference link table? I know that at least half of the 150+ referenced articles are available on my site somewhere or here at the Hive, but not exactly where... If you can tell me which reference is found where, I'll add hyperlinks to them from within the review.) ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 06-08-04 00:46 No 512099				Varma&Kabalka: Cr(II) Nitrostyrene Reduction (Rated as: excellent)
						Chromium(II) Chloride Reduction of Nitrostyrenes: A Facile Route to Oximes Rajender S. Varma, Manju Varma and George W. Kabalka Synthetic Communications 15(14), 1325-1332 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2oxime.crcl2.html) Abstract α,β-Unsaturated nitroalkenes are rapidly reduced by chromium(II) chloride to oximes. ____ ___ __ _ Chromium(II) Chloride Reduction of Nitroalkenes: A Facile Route to Carbonyl Compounds Rajender S. Varma, Manju Varma and George W. Kabalka Tetrahedron Letters 26(32), 3777-3778 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2ketone.crcl2.html) Abstract α,β-Unsaturated nitroalkenes are readily reduced by chromium(II) chloride to the corresponding carbonyl compounds in good yields. _{This article has been posted before in Post 244992 (foxy2: "Chromium(II)Chloride Reduction of Nitroalkenes", Chemistry Discourse)} ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 06-11-04 10:30 No 512771				Nitroalkene Reactions (Rated as: good read)
						Conjugated nitroalkenes: versatile intermediates in organic synthesis Anthony G. M. Barrett, Gregory G. Graboski Chem. Rev. 86, 751-762 (1986) (https://www.rhodium.ws/pdf/conjugated.nitroalkenes.review.pdf) ____ ___ __ _ _{Reactions of Sodium Borohydride in Acidic Media. V.} Reduction and Alkylation of Oximes with Carboxylic Acids; A New Synthesis of N,N-Dialkylhydroxylamines Gribble, Gordon W.; Leiby, Robert W.; Sheehan, Myles N. Synthesis 856-859 (1977) (https://www.rhodium.ws/pdf/oxime2hydroxylamine.nabh4-rcooh.pdf) ____ ___ __ _ Reduction of nitroalkenes to nitroalkanes with aqueous sodium borohydride Albert I. Meyers, J. C. Sircar J. Org. Chem. 32, 4134-4136 (1967) (https://www.rhodium.ws/pdf/nitroalkenes.aq-nabh4.pdf) ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 09-03-04 16:51 No 529378				CdCl2–Mg–H2O: Nitroalkenes to Keto-compounds (Rated as: good read)
						Cadmium Chloride–Magnesium–Water: A New System for Regioselective Transformation of Conjugated Nitroalkenes to Ketocompounds Manobjyoti Bordoloi J. Chem. Soc. Chem. Commun. 922-923 (1993) (https://www.rhodium.ws/chemistry/nitroalkene2ketone.mg-cdcl2.html) Abstract Reaction of 6-nitro-Δ5-steroids and nitroalkenes in tetrahydrofuran with CdCl₂–Mg–H₂O furnished 6-ketosteroids and ketocompounds, respectively, in good yield. ^{The Hive - Clandestine Chemists Without Borders}



		java (Hive Addict) 09-05-04 22:25 No 529755				Some of R.S.Varma's recent work's........
						R.S. Varma, Green Chem. 1, 43-55 (1999) R.S. Varma, J. Heterocyclic Chem. 35, 1565-1571 (1999) R.S. Varma, Pure Appl. Chem. 73, 193-198 (2001) R.S. Varma, Tetrahedron Report # 598, Tetrahedron 58, 1235-55 (2002) U. Pillai, E. Sahle-Demessie and R.S. Varma, J. Mat. Chem. 12, 3199 (2002) R.S. Varma, in Microwaves in Organic Synthesis (A. Loupy, Ed.), Chapter 6, pp 181-218, Wiley-VCH, Weinheim (2002). R.S. Varma, Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation AstraZeneca Research Foundation India, Bangalore, India (2002) ^{(Free copy available on request from: azrefi@astrazeneca.com)} R.S. Varma, In: Ionic Liquids as Green Solvents. Progress and Prospects, R. Rogers and K. R. Seddon (Eds.), ACS Symposium Series 856, American Chemical Society, Washington, D. C., Chapter 7, pp 82-92 (2003). R.S. Varma, Microwave Technology-Chemical Applications: Kirk-Othmer Encyclopedia of Chemical Technology, 5th Ed (2004). Y. Ju and R.S. Varma, Green Chem. 6, 219 (2004) It is better to die on your feet than to live on your knees....... -Emiliano Zapata-



		indole_amine (Hive Bee) 09-30-04 04:02 No 533836				Reactions promoted by Microwaves and Clays (Rated as: excellent)
						Clay and clay-supported reagents in organic synthesis Rajender S. Varma Tetrahedron 58 (2002) p.1235-1255 An overview over the possibilities and applications of different clays in organic chemistry. Solventfree reductive aminations of carbonyl compounds on clay, oxidations of alcohols to carbonyls by clayfen, conversions of aldehydes to nitriles, synthesis of imines and enamines, Friedel-Crafts, Diels-Alder, Suzuki and Heck arylation reactions can be done using clay reagents, as well as dehydrations, isomerizations and addition reactions... Selective Nitration of Styrenes with Clayfen and Clayan: A Solvent-free Synthesis of β-Nitrostyrenes Varma, Rajender S.; Naicker, Kannan P.; Liesen, Per J. Tetrahedron Letters 39, 23 (1998) pp. 3977-3980 Abstract A facile, solvent-free synthesis of beta-nitrostyrenes is described from styrene and its substituted derivatives using inexpensive "doped" clay reagents, clayfen and clayan. Looks useful for arriving at ketones in connection with Post 458467 (Rhodium: "Oximes from Nitroalkenes using Decaborane CTH", Novel Discourse) Solid State Regeneration of Ketones from Oximes on Wet Silica Supported Sodium Periodate Using Microwaves Varma, Rajender S.; Dahiya, Rajender; Saini, Rajesh K. Tetrahedron Letters 38, 51 (1997) pp. 8819-8820 Abstract Microwave irradiation of ketoximes on wet silica supported sodium periodate under solvent-free conditions provides a fast, efficient and simple method for regeneration of ketones. Clay catalyzed synthesis of imines and enamines under solvent-free conditions using microwave irradiation (Varma, Rajender S.; Dahiya, Rajender; Kumar, Sudhir) Tetrahedron Letters 38, 12 (1997) pp. 2039-2042 Abstract The reactions of primary and secondary amines with aldehydes and ketones, respectively, are accelereated by microwaves under solvent-free conditions in the presence of montmorillonite K 10 clay to afford a high yield synthesis of imines and enamines. Microwave-assisted oxidation of alcohols under solvent-free conditions using clayfen (Varma, Rajender S.; Dahiya, Rajender) Tetrahedron Letters 38, 12 (1997) pp. 2043-2044 Abstract Adsorbed on clayfen, alcohols are readily oxidized to carbonyl compounds upon exposure to microwaves under solvent-free conditions. Tis rapid, selective and environmentally benign method conserves the use of excess solvents and toxic antioxidants usually employed. And this transformation can also be undone... Microwave-Assisted Reduction of Carbonyl Compounds in Solid State Using Sodium Borohydride Supported on Alumina (Varma, Rajender S.; Saini, Rajesh K.) Tetrahedron Letters 38, 25 (1997) pp. 4337-4338 Abstract A manipulatively simple and rapid method for the reduction of carbonyl compounds is described that is conducted under solventless "dry" conditions using NaBH₄/alumina and microwave irradiation.

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