Print Page - Oximes from Nitroalkenes using Decaborane CTH

Title: Oximes from Nitroalkenes using Decaborane CTH
Post by: Rhodium on September 11, 2003, 02:23:00 PM

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.thevespiary.org/rhodium/Rhodium/chemistry/cth.nitroalkene2oxime.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/cth.nitroalkene2oxime.html)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_5u0s.gif)

Abstract

?,?-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.

Title: Hypophosphite CTH: Nitroalkenes to Oximes
Post by: Rhodium on May 26, 2004, 06:18:00 PM

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.thevespiary.org/rhodium/Rhodium/chemistry/cth.ns2oxime.pd-na-hypo.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/cth.ns2oxime.pd-na-hypo.html)

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

Title: To bees with access to literature
Post by: Aurelius on May 26, 2004, 07:28:00 PM

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!

:P

Title: Varma vs. Kabalka
Post by: Rhodium on May 26, 2004, 10:23:00 PM

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 (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.

Title: Varma & Kabalka: Nitroalkene Reduction Review
Post by: Rhodium on May 27, 2004, 07:48:00 PM

Selected Reductions of Conjugated Nitroalkenes
George W. Kabalka, Laila H. M. Guindi and Rajender S. Varma

Tetrahedron 46(21), 7443-7457 (1990) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrostyrene.reduction.review.html)

(https://www.thevespiary.org/rhodium/Rhodium/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.

Title: Nitroalkene Synthesis & Reduction Review
Post by: Rhodium on May 30, 2004, 10:54:00 AM

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.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene.synthesis-reduction.review.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene.synthesis-reduction.review.html)

Table of Contents
I. Introduction
II. Preparation of Conjugated Nitroalkenes
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)A. From Carbonyl Compounds
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)B. From Alkenes
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)C. Miscellaneous Methods
III. Reduction of Conjugated Nitroalkenes
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)A. Preparation of Nitroalkanes
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)B. Preparation of Oximes
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)C. Preparation of Carbonyl Compounds
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000458467-file_oxgw.gif)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.)

Title: Varma&Kabalka: Cr(II) Nitrostyrene Reduction
Post by: Rhodium on June 07, 2004, 05:46:00 PM

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.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2oxime.crcl2.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2oxime.crcl2.html)

Abstract
?,?-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.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2ketone.crcl2.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2ketone.crcl2.html)

Abstract
?,?-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 (https://www.thevespiary.org/talk/index.php?topic=7382.msg24499200#msg24499200)
(foxy2: "Chromium(II)Chloride Reduction of Nitroalkenes", Chemistry Discourse)}

Title: Nitroalkene Reactions
Post by: Rhodium on June 11, 2004, 03:30:00 AM

Conjugated nitroalkenes: versatile intermediates in organic synthesis
Anthony G. M. Barrett, Gregory G. Graboski

Chem. Rev. 86, 751-762 (1986) (https://www.thevespiary.org/rhodium/Rhodium/pdf/conjugated.nitroalkenes.review.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/pdf/oxime2hydroxylamine.nabh4-rcooh.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/pdf/nitroalkenes.aq-nabh4.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/nitroalkenes.aq-nabh4.pdf)

Title: CdCl2–Mg–H2O: Nitroalkenes to Keto-compounds
Post by: Rhodium on September 03, 2004, 09:51:00 AM

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.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2ketone.mg-cdcl2.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitroalkene2ketone.mg-cdcl2.html)

Abstract
Reaction of 6-nitro-?5-steroids and nitroalkenes in tetrahydrofuran with CdCl₂–Mg–H₂O furnished 6-ketosteroids and ketocompounds, respectively, in good yield.

Title: Some of R.S.Varma's recent work's........
Post by: java on September 05, 2004, 03:25:00 PM

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)

Title: Reactions promoted by Microwaves and Clays
Post by: indole_amine on September 29, 2004, 09:02:00 PM

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