The Vespiary

The Hive => Chemistry Discourse => Topic started by: sYnThOmAtIc on April 15, 2003, 05:16:00 AM

Title: revdrone reduction contest references???
Post by: sYnThOmAtIc on April 15, 2003, 05:16:00 AM

Electrolytic reductions.

Ok I know alot of people participated in the contest and surely somebody has copies of the procedures on hand???

WEll if anybody has access to any of the reduction methods listed below that have references to electrolytic reduction please post them when it is convient for you if it isn't too much trouble to get them and post them. You can omit some of the standard chemical process to save room or time as I'm only interested in the electrochemical methods.

Reaction Classification Preparation
Reagent ethanol
acetic acid
aqueous sulfuric acid
Other conditions Electrolysis.an einer Quecksilber-Kathode
Ref. 1 2252728; Journal; Alles; JACSAT; J.Amer.Chem.Soc.; 54; 1932; 271,273;

Reaction Classification Preparation
Reagent ethanol
acetic acid
aqueous hydrochloric acid
Other conditions Electrolysis
Ref. 1 532257; Journal; Bruckner; JLACBF; Justus Liebigs Ann. Chem.; 518; 1935; 226, 242;

Reaction Classification Preparation
Reagent lead-cathode
acetic acid
aqueous hydrochloric acid
Other conditions Electrolysis
Ref. 1 532130; Journal; Kondo; Kataoka; ITKNA6; Itsuu Kenkyusho Nempo; 2; 1951; 7, 10; engl. Ref. S. 43, 48; Chem.Abstr.; 1953; 7519;

Reaction Classification Preparation
Reagent lead-cathode
ethanol
acetic acid
Other conditions Electrolysis.Reagens 4: wss. Salzsaeure
Ref. 1 532128; Journal; Schultz; Arnold; JACSAT; J.Amer.Chem.Soc.; 71; 1949; 1911, 1913;
Ref. 2 532129; Journal; Slotta; Haberland; ANCEAD; Angew.Chem.; 46; 1933; 766, 769;

Reaction Classification Chemical behaviour
Other conditions Electrolysis
Ref. 1 1705573; Journal; Kondo; Ishiwata; CHBEAM; Chem.Ber.; 64; 1931; 1533, 1636;

Reaction Classification Preparation
Other conditions Electrolysis
Ref. 1 532307; Journal; Sugasawa; Hino; PHBUA9; Pharm.Bull.; 2; 1954; 242, 245

Reaction Classification Preparation
Reagent 0.3 M H2SO4
Solvent propan-2-ol
H2O
Yield 60. (BRN507867)
Temperature 10 - 15 øC
Other conditions electrolysis
Ref. 1 5601939; Journal; Wessling, Michael; Schaefer, Hans J.; CHBEAM; Chem.Ber.; EN; 124; 10; 1991; 2303-2306;

Reaction Classification Preparation
Reagent 1 N H2SO4
Solvent acetonitrile
H2O
Other conditions electrolysis; pH1.16
Ref. 1 5663729; Journal; Marcot, Bernard; Rabaron, Alain; Viel, Claude; Bellec, Christian; Deswarte, Stephane; Maitte, Pierre; CJCHAG; Can.J.Chem.; FR; 59; 1981; 1224-1234

Reaction Classification Preparation
Other conditions (electrochemical reduction)
Ref. 1 16508; Journal; Bessho,K.; CPBTAL; Chem.Pharm.Bull.; EN; 11; 1963; 1500-1503

Reaction Classification Preparation
Reagent aq. HCl, AcOH
Solvent tetrahydrofuran
methanol
Other conditions (electrochemical reduction)
Ref. 1 16506; Journal; Bessho,K.; CPBTAL; Chem.Pharm.Bull.; EN; 11; 1963; 1491-1494;

Title: It's been a while but I tried to go through as
Post by: moo on April 15, 2003, 06:05:00 AM

It's been a while but I tried to go through as many of these refs as possible. I recall most of them aren't that good... The outstanding ones in my opinion are

Post 47461 (https://www.thevespiary.org/talk/index.php?topic=11427.msg4746100#msg4746100)

(uemura: "Electrochemical Reduction of Nitrostyrenes", Novel Discourse) (There are few >70% yielding nitrostyrene reductions from that era) and

Patent GB2122617 (http://l2.espacenet.com/dips/viewer?PN=GB2122617&CY=gb&LG=en&DB=EPD)

(they figured out the right tricks, eg. NH₂OH. This ref is the way to go for high yields). I'll have another look at the library just to make sure this was the case and let you know if there's anything special. UTFSE throughly, at least one of the refs is here already:

Post 421272 (https://www.thevespiary.org/talk/index.php?topic=6888.msg42127200#msg42127200)

(Vitus_Verdegast: "electrochemical reduction of nitroalkenes", Chemistry Discourse).

Title: If I remember correctly, I put all really...
Post by: Lilienthal on April 15, 2003, 09:34:00 PM

If I remember correctly, I put all really important refs from that discussion onto my references list on my homepage.

Title: Lilienthal's References
Post by: Rhodium on April 15, 2003, 09:49:00 PM

That reference list, does it represent your reccommendations or your collection?

Title: Well, after checking out what I could I dare...
Post by: moo on April 16, 2003, 04:06:00 PM

Well, after checking out what I could I dare say that everything important from this list is already here. I consider important references those that give details about performing the electrolysis, not just the usual stuff about dissolving the compound in acidic solvent in the cathode compartment and electrolysing and so on. Also Can. J. Chem. 59, 1224-1234 (1981) has next to nothing to do with nitrostyrene reductions, it seems Drone was in a bit of hurry from time to time. ;D

Title: Drone's Tactic
Post by: Rhodium on April 17, 2003, 01:28:00 AM

Drone usually performed beilstein searches looking for desirable transformations, without necessarily checking each and every reference manually each time he posted a reference list.

Title: Every article I made copies off are on that...
Post by: Lilienthal on April 17, 2003, 05:44:00 PM

Every article I made copies off are on that list. You may see this as a recommendation if you want, usually there were not many copy-worth articles in Drone's lists...