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silenziox
(Stranger)
10-26-03 17:00
No 466868
Sonochemistry, reductions

Here are couple of excellent publications of sonication links:

1. Petrier C.; Suslick, K. S. "Ultrasound-Enhanced Reactivity Of Calcium In The Reduction Of Aromatic Hydrocarbons" Ultrasonics Sonochemistry 2000, 7, 53-61. (http://www.scs.uiuc.edu/suslick/pdf/uss0053.pdf) Typical reaction is carried under an argon atmosphere and the cleanup after the reduction looks tedious, but I think it's worth of it. Tert-butanol were used as hydrogen donor and the isolated yields were great. As this reaction is done with sonication device connected to the reaction flask, I wonder could it beconverted for more cheaper "normal" ultrasonic bath cleaner?

2. - Suslick, K. S.; Casadonte, D. J. "Heterogeneous Sonocatalysis with Nickel Powder" J. Am. Chem. Soc. 1987, 109, 3459-3461. (http://www.scs.uiuc.edu/suslick/pdf/jacs873459.pdf)
"However, when using Nickel powder as catalyst, no reduction of ketones or aldehydes was observed".
"Compared to Raney Ni, however, our activated Ni-powder is more selective (C-O double bonds are untouched).
Reaction runs at 273K with 1atm H2. Octane was used as solvent. Interesting indeed.
It should work with nitrostyrenes then, which makes this shit cheap as hell cool

...

My dream:
-Nitroalkene with ultrasound (https://www.rhodium.ws/chemistry/nitrostyrene.ultrasound.html)
modified to produce DL-threo-substituted-nitroalkenes for optical resolution (https://www.rhodium.ws/chemistry/norpseudoephedrine.html)
- Collecting the nitromethane/nitroethane and nitroalkene using rotovap, recrystallation of the nitroalkene - reduction of the nitroalkene with either:
1. calcium as sonocatalyst,
2. Ni-powder as sonocatalyst,
3. Pd/C as sonocatalyst (much less Pd/C to use?)
- resolving the reduced nitroalkene into optically pure isomers
- converting the inactive isomer into active one by oxidation and re-amination etc.
- other workup as the favoured compound requires smile

Yields should be quite appealing wink

Better overdose than lowerdose

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	All posts		Subject: Sonochemistry, reductions		Please login to post


		silenziox (Stranger) 10-26-03 17:00 No 466868				Sonochemistry, reductions
						Here are couple of excellent publications of sonication links: 1. Petrier C.; Suslick, K. S. "Ultrasound-Enhanced Reactivity Of Calcium In The Reduction Of Aromatic Hydrocarbons" Ultrasonics Sonochemistry 2000, 7, 53-61. (http://www.scs.uiuc.edu/suslick/pdf/uss0053.pdf) Typical reaction is carried under an argon atmosphere and the cleanup after the reduction looks tedious, but I think it's worth of it. Tert-butanol were used as hydrogen donor and the isolated yields were great. As this reaction is done with sonication device connected to the reaction flask, I wonder could it beconverted for more cheaper "normal" ultrasonic bath cleaner? 2. - Suslick, K. S.; Casadonte, D. J. "Heterogeneous Sonocatalysis with Nickel Powder" J. Am. Chem. Soc. 1987, 109, 3459-3461. (http://www.scs.uiuc.edu/suslick/pdf/jacs873459.pdf) "However, when using Nickel powder as catalyst, no reduction of ketones or aldehydes was observed". "Compared to Raney Ni, however, our activated Ni-powder is more selective (C-O double bonds are untouched). Reaction runs at 273K with 1atm H2. Octane was used as solvent. Interesting indeed. It should work with nitrostyrenes then, which makes this shit cheap as hell ... My dream: -Nitroalkene with ultrasound (https://www.rhodium.ws/chemistry/nitrostyrene.ultrasound.html) modified to produce DL-threo-substituted-nitroalkenes for optical resolution (https://www.rhodium.ws/chemistry/norpseudoephedrine.html) - Collecting the nitromethane/nitroethane and nitroalkene using rotovap, recrystallation of the nitroalkene - reduction of the nitroalkene with either: 1. calcium as sonocatalyst, 2. Ni-powder as sonocatalyst, 3. Pd/C as sonocatalyst (much less Pd/C to use?) - resolving the reduced nitroalkene into optically pure isomers - converting the inactive isomer into active one by oxidation and re-amination etc. - other workup as the favoured compound requires Yields should be quite appealing Better overdose than lowerdose

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