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All 6 posts Subject: Ion exchange resin-borohydride Please login to post Down

Barium
(Hive Bee)
11-29-02 15:33
No 384596
      Ion exchange resin-borohydride
(Rated as: excellent)

Synthetic Communications, 19 (5&6), 805-811 (1989)

The reduction of alpha, beta-unsaturated nitroalkenes to nitroalkanes with borohydride supported on an ion exchange resin

Authors: Goudgaon, Wadgaonkar and Kabalka

...We wish to report that nitroalkenes are selectively reduced to nitroalkanes by borohydride supported on an ion exchange resin in MeOH at room temperature. Borohydride bound resin was prepared by stirring commercially avaliable anion exchange resin, Amberlite IRA-400 (Cl^- form) with aqueous sodium borohydride solution. The reaction procedure involves the addition of borohydride ion exchange resin to a methanolic solution of the nitroalkene. The reactions are complete in 60 minutes and can be monitored by TLC (and in some cases by the disapperance of the yellow color of the nitroalkene). The product nitroalkanes are isolated by removal of the ion exchange resin by filtration and evaporatin of the filtrate under reduced pressure. The resin may be reused by rinsing the spent material with dilute hydrochloric acid followed by regeneration with aqueous sodium borohydride solution.

Procedures:

Borohydride bound ion exchange resin

An aqueous solution of sodium borohydride (0,5 M, 100 ml) was stirred with 10 g of wet chloride form resin (Amberlite IRA-400) for one hour. The resulting resin was washed thoroughly with distilled water until free from excess sodium borohydride. The borohydride bound exchange resin was dried in vacuo at 65°C for 5 hours. The dried resin was analyzed for borohydride content by hydrogen evolution on acidification with 0,05 N HCl; the average capacity of the ion exchange resin was found to be 2,5 mmol BH₄^-/g of resin.

General procedure for the synthesis of nitroalkanes

The preparation of 2-(2-nitropropyl)thiophene is representative of the procedure employed. 2-(2-Nitropropenyl)thiophene (2 mmol 0,338 g) was dissolved in MeOH (40 ml) in a 100 ml Erlenmeyer flask containing a magnetic stirring bar. Borohydride supported ion exchange resin (2,2 mmol, 0,88 g) was then added at room temperature to the well stirred solution. A mildely exothermic reaction ensued with the gradual disapperance of the yellow coloration. The reaction mixture was stirred for 60 minutes at room temperature and the the resin was filtered off, washed twice with MeOH (2x10 ml). Removal of the MeOH under reduced pressure yielded 0,265 g (78%) of pure 2-(2-nitropropyl)thiophene as an oil.

Nitrocyclohexene --> Nitrocyclohexane 80%
2-Nitro-1-phenylpropene --> 2-Nitro-1-phenylpropane 81%
2-Nitro-1-(p-bromophenyl)-propene --> 2-Nitro-1-(p-bromophenyl)-propane 80%
2-Nitro-1-(3,4-diethoxyphenyl)-propene --> 2-Nitro-1-(3,4-diethoxyphenyl)-propane 83%
Catalytic hydrogenation freak

GC_MS
(Hive Bee)
11-29-02 15:46
No 384598
User Picture       kabalka

Goudgaon, Wadgaonkar and Kabalka

Kabalka's group did alot of research on beta-nitrostyrenes. Their aim was to synthesize labelled amphetamines fast and easy. There is a nice review from his group, more like a compendium of their work, showing possible interconversion possibilities for nitroalkanes, nitroalkenes, oximes etc. It appeared in Tetrahedron, but I haven't got the reference handy... When I looked for it in TFSE, it was mentioned several times.
Anyway, this is another nice contribution from our good old friend Ba wink
Ave Hive, synthetisandi te salutant!

Barium
(Hive Bee)
11-29-02 16:03
No 384600
      I believe this is the one you mean.

I believe this is the one you mean.

Tetrahedron, vol., 46, No. 21, pp. 7443-7457, 1990
Selected reductions of conjugated nitroalkenes
Catalytic hydrogenation freak

GC_MS
(Hive Bee)
11-29-02 16:26
No 384605
User Picture       .

I believe this is the one you mean.

yeps smile
Ave Hive, synthetisandi te salutant!

Rhodium
(Chief Bee)
11-29-02 17:09
No 384614
      Varma & Kabalka Rulez!

https://www.rhodium.ws/chemistry/nitrostyrene.reduction.ber.html

Rhodium
(Chief Bee)
06-01-04 05:33
No 510662
User Picture       Varma & Kabalka: Nitroalkene -BH4-> Nitroalkane
(Rated as: excellent)

Selective Reduction of Nitroalkenes with Methanolic Sodium Borohydride: A Facile Route To Nitroalkanes
Rajender S. Varma and George W. Kabalka
Synthetic Communications, 15(2), 151-155 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2nitroalkane.v-k.nabh4.html)

Abstract
α,β-Unsaturated nitroalkenes are rapidly and selectively reduced at room temperature to nitroalkanes in high yields by sodium borohydride in a tetrahydrofuran-methanol solvent system.
____ ___ __ _

The Reduction of Nitroalkenes to Nitroalkanes with Borohydride Exchange Resin
N.M. Goudgaon, P.P. Wadgaonkar and G.W. Kabalka
Synthetic Communications, 19(5-6), 805-811 (1989) (https://www.rhodium.ws/chemistry/nitroalkene2nitroalkane.v-k.ber.html)

Abstract
Borohydride supported on an ion exchange resin selectively reduced α,β-unsaturated nitroalkenes to nitroalkanes in high yields. The isolation of pure products by simple filtration is a key feature of this method.

^{The Hive - Clandestine Chemists Without Borders}

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	All 6 posts		Subject: Ion exchange resin-borohydride		Please login to post		Down


		Barium (Hive Bee) 11-29-02 15:33 No 384596				Ion exchange resin-borohydride (Rated as: excellent)
						Synthetic Communications, 19 (5&6), 805-811 (1989) *The reduction of alpha, beta-unsaturated nitroalkenes to nitroalkanes with borohydride supported on an ion exchange resin* Authors: Goudgaon, Wadgaonkar and Kabalka ...We wish to report that nitroalkenes are selectively reduced to nitroalkanes by borohydride supported on an ion exchange resin in MeOH at room temperature. Borohydride bound resin was prepared by stirring commercially avaliable anion exchange resin, Amberlite IRA-400 (Cl^- form) with aqueous sodium borohydride solution. The reaction procedure involves the addition of borohydride ion exchange resin to a methanolic solution of the nitroalkene. The reactions are complete in 60 minutes and can be monitored by TLC (and in some cases by the disapperance of the yellow color of the nitroalkene). The product nitroalkanes are isolated by removal of the ion exchange resin by filtration and evaporatin of the filtrate under reduced pressure. The resin may be reused by rinsing the spent material with dilute hydrochloric acid followed by regeneration with aqueous sodium borohydride solution. Procedures: Borohydride bound ion exchange resin An aqueous solution of sodium borohydride (0,5 M, 100 ml) was stirred with 10 g of wet chloride form resin (Amberlite IRA-400) for one hour. The resulting resin was washed thoroughly with distilled water until free from excess sodium borohydride. The borohydride bound exchange resin was dried in vacuo at 65°C for 5 hours. The dried resin was analyzed for borohydride content by hydrogen evolution on acidification with 0,05 N HCl; the average capacity of the ion exchange resin was found to be 2,5 mmol BH₄^-/g of resin. General procedure for the synthesis of nitroalkanes The preparation of 2-(2-nitropropyl)thiophene is representative of the procedure employed. 2-(2-Nitropropenyl)thiophene (2 mmol 0,338 g) was dissolved in MeOH (40 ml) in a 100 ml Erlenmeyer flask containing a magnetic stirring bar. Borohydride supported ion exchange resin (2,2 mmol, 0,88 g) was then added at room temperature to the well stirred solution. A mildely exothermic reaction ensued with the gradual disapperance of the yellow coloration. The reaction mixture was stirred for 60 minutes at room temperature and the the resin was filtered off, washed twice with MeOH (2x10 ml). Removal of the MeOH under reduced pressure yielded 0,265 g (78%) of pure 2-(2-nitropropyl)thiophene as an oil. Nitrocyclohexene --> Nitrocyclohexane 80% 2-Nitro-1-phenylpropene --> 2-Nitro-1-phenylpropane 81% 2-Nitro-1-(p-bromophenyl)-propene --> 2-Nitro-1-(p-bromophenyl)-propane 80% 2-Nitro-1-(3,4-diethoxyphenyl)-propene --> 2-Nitro-1-(3,4-diethoxyphenyl)-propane 83% Catalytic hydrogenation freak



		GC_MS (Hive Bee) 11-29-02 15:46 No 384598				kabalka
						Goudgaon, Wadgaonkar and Kabalka Kabalka's group did alot of research on beta-nitrostyrenes. Their aim was to synthesize labelled amphetamines fast and easy. There is a nice review from his group, more like a compendium of their work, showing possible interconversion possibilities for nitroalkanes, nitroalkenes, oximes etc. It appeared in Tetrahedron, but I haven't got the reference handy... When I looked for it in TFSE, it was mentioned several times. Anyway, this is another nice contribution from our good old friend Ba Ave Hive, synthetisandi te salutant!



		Barium (Hive Bee) 11-29-02 16:03 No 384600				I believe this is the one you mean.
						I believe this is the one you mean. Tetrahedron, vol., 46, No. 21, pp. 7443-7457, 1990 Selected reductions of conjugated nitroalkenes Catalytic hydrogenation freak



		GC_MS (Hive Bee) 11-29-02 16:26 No 384605				.
						I believe this is the one you mean. yeps Ave Hive, synthetisandi te salutant!



		Rhodium (Chief Bee) 11-29-02 17:09 No 384614				Varma & Kabalka Rulez!
						https://www.rhodium.ws/chemistry/nitrostyrene.reduction.ber.html



		Rhodium (Chief Bee) 06-01-04 05:33 No 510662				Varma & Kabalka: Nitroalkene -BH4-> Nitroalkane (Rated as: excellent)
						Selective Reduction of Nitroalkenes with Methanolic Sodium Borohydride: A Facile Route To Nitroalkanes Rajender S. Varma and George W. Kabalka Synthetic Communications, 15(2), 151-155 (1985) (https://www.rhodium.ws/chemistry/nitroalkene2nitroalkane.v-k.nabh4.html) Abstract α,β-Unsaturated nitroalkenes are rapidly and selectively reduced at room temperature to nitroalkanes in high yields by sodium borohydride in a tetrahydrofuran-methanol solvent system. ____ ___ __ _ The Reduction of Nitroalkenes to Nitroalkanes with Borohydride Exchange Resin N.M. Goudgaon, P.P. Wadgaonkar and G.W. Kabalka Synthetic Communications, 19(5-6), 805-811 (1989) (https://www.rhodium.ws/chemistry/nitroalkene2nitroalkane.v-k.ber.html) Abstract Borohydride supported on an ion exchange resin selectively reduced α,β-unsaturated nitroalkenes to nitroalkanes in high yields. The isolation of pure products by simple filtration is a key feature of this method. ^{The Hive - Clandestine Chemists Without Borders}

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