Action of alkali metals in liquid ammonia on substituted thiophenes. Communication 9. Preparation of 5-mercapto-4-ketoalkanoic acids by reductive cleavage of 4-acetylamino- and 4-nitrothiophene-2-carboxylic acids

1984 ◽  
Vol 33 (10) ◽  
pp. 2136-2139
Author(s):  
Ya. L. Gol'dfarb ◽  
E. P. Zakharov ◽  
F. M. Stoyanovich ◽  
M. A. Marakatkina
Keyword(s):  
Carboxylic Acids ◽  
Alkali Metals ◽  
Liquid Ammonia ◽  
Reductive Cleavage

Reactions of aliphatic halides with solutions of alkali metals in liquid ammonia: I. Experiments with alkyl halides

2010 ◽  
Vol 81 (12) ◽  
pp. 1033-1052 ◽  
Author(s):  
A. Beverloo ◽  
M. C. Dieleman ◽  
P. E. Verkade ◽  
K. S. de Vries ◽  
B. M. Wepster
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia ◽  
Alkyl Halides

Steric Course of the Reduction of Ketoacetal Esters with Alkali Metals in Liquid Ammonia

1979 ◽  
Vol 18 (8) ◽  
pp. 637-638 ◽  
Author(s):  
Fritz Jaisli ◽  
Daniel Sternbach ◽  
Albert Eschenmoser ◽  
Masayuki Shibuya
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia

Visible-light-mediated catalytic decarboxylative alkylation of 2-pyridone derivatives via a C3-selective C–H functionalization

2021 ◽  
Author(s):  
Worawat Niwetmarin ◽  
Rungroj Saruengkhanphasit ◽  
Chatchakorn Eurtivong ◽  
Somsak Ruchirawat
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Reductive Cleavage ◽  
Alkyl Radicals

A direct C–H functionalization approach to access C3-alkylated 2-pyridone derivatives is reported. This study utilizes N-hydroxyphthalimide (NHPI) esters of various carboxylic acids as sources for alkyl radicals by reductive cleavage...

REDUCTIVE CLEAVAGE WITH METAL IN LIQUID AMMONIA: I. THE SELECTIVE CLEAVAGE OF THE BENZYLTHIO C—S BOND VERSUS THE BENZYLIDENEDIOXY C—O BOND IN METHYL S-BENZYL-4,6-O-BENZYLIDENE-2-THIO-α-D-ALTROPYRANOSIDES; THE INFLUENCE OF THE COSOLVENT 1,2-DIMETHOXYETHANE ON THE COURSE OF THE REACTION

1966 ◽  
Vol 44 (5) ◽  
pp. 591-602 ◽  
Author(s):  
U. G. Nayak ◽  
R. K. Brown
Keyword(s):  
Infrared Absorption ◽  
Liquid Ammonia ◽  
Reductive Cleavage ◽  
The Other ◽  
Metallic Sodium ◽  
Absorption Bands ◽  
Strong Band ◽  
The One ◽  
Infrared Absorption Bands ◽  
Phenyl Moiety

The improved solubility of methyl S-benzyl-4,6-O-benzylidene-2-thio-α-D-altropyranoside (1) in liquid ammonia diluted with 1,2-dimethoxyethane has permitted the selective cleavage by metallic sodium or lithium of the C—S bond to give methyl 4,6-O-benzylidene-2-thio-α-D-altropyranoside in 70–75% yield. On the other hand, the slight solubility of I in liquid ammonia alone results only in the completely hydrogenolyzed material, methyl 2-thio-α-D-altropyranoside, along with unchanged I.Generally, in liquid ammonia alone, reductive cleavage is rapid (15–20 min) and the benzylidene and benzyl groups are converted largely into toluene accompanied by a small amount of bibenzyl. In liquid ammonia – 1,2-dimethoxyethane mixtures the reaction is much slower (≥ 1.5 h); under these conditions the benzylidene and benzyl groups are converted to a larger extent into bibenzyl, the rest becoming toluene.The two strong infrared absorption bands (in Nujol) in the region of 766 to 778 cm−1 and 706 to 718 cm−1 have been assigned to the phenyl moiety of the benzylidene group, and the one strong band in the region of 702 cm−1 to the phenyl moiety of the S-benzyl group.

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