Oxidation of vicinal diols to .alpha.-dicarbonyl compounds by trifluoroacetic anhydride-activated dimethyl sulfoxide

1987 ◽  
Vol 52 (22) ◽  
pp. 4851-4855 ◽  
Author(s):  
Catherine M. Amon ◽  
Martin G. Banwell ◽  
G. Lance Gravatt
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride ◽  
Dicarbonyl Compounds ◽  
Vicinal Diols

ChemInform Abstract: DIMETHYL SULFOXIDE-TRIFLUOROACETIC ANHYDRIDE. NEW REAGENT FOR OXIDATION OF ALCOHOLS TO CARBONYLS

1976 ◽  
Vol 7 (26) ◽  
pp. no-no
Author(s):  
K. OMURA ◽  
A. K. SHARMA ◽  
D. SWERN
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride ◽  
Oxidation Of Alcohols

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides

2016 ◽  
Vol 69 (1) ◽  
pp. 61 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis
Keyword(s):  
Ethyl Acetate ◽  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Acid ◽  
Sulfonic Acid ◽  
Trifluoroacetic Anhydride ◽  
Ring Cleavage ◽  
Thermal Rearrangement ◽  
Heterocyclic Synthesis ◽  
Similar Treatment ◽  
Catalytic Hydrogenolysis

Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

Dimethyl sulfoxide-trifluoroacetic anhydride. New reagent for oxidation of alcohols to carbonyls

1976 ◽  
Vol 41 (6) ◽  
pp. 957-962 ◽  
Author(s):  
Kanji. Omura ◽  
Ashok K. Sharma ◽  
Daniel. Swern
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride ◽  
Oxidation Of Alcohols

scholarly journals SYNTHESIS OF ULOSES BY THE OXIDATION WITH DIMETHYL SULFOXIDE-TRIFLUOROACETIC ANHYDRIDE

1977 ◽  
Vol 6 (11) ◽  
pp. 1327-1330 ◽  
Author(s):  
Juji Yoshimura ◽  
Ken-ichi Sato ◽  
Hironobu Hashimoto
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride

scholarly journals Reaction of Dimethyl Sulfoxide–Trifluoroacetic Anhydride with Anilines, Phenols, and Thiophenols

1977 ◽  
Vol 50 (2) ◽  
pp. 447-452 ◽  
Author(s):  
Yuji Hiraki ◽  
Masahiro Kamiya ◽  
Rikuhei Tanikaga ◽  
Noboru Ono ◽  
Aritsune Kaji
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride

Thiomethoxymethylation of 5-Aryloxytetrazoles via Modified Swern Reagents

2005 ◽  
Vol 2005 (3) ◽  
pp. 202-204
Author(s):  
Hossein A. Dabbagh ◽  
Ali Bagheri
Keyword(s):  
Dimethyl Sulfoxide ◽  
Electronic Effect ◽  
Oxalyl Chloride ◽  
Trifluoroacetic Anhydride ◽  
Reaction Conditions ◽  
Swern Oxidation

The modified Swern oxidation of 5-aryloxytetrazole (Ar- = 4-NO2-C6H4-, C6H5-, 2,6-dimethoxy-C6H3-) rings is described using combination of dimethyl sulfoxide with dicyclohexylcarbodiimide (DCC), oxalyl chloride or trifluoroacetic anhydride. The product observed at 1- and/or 2-position of tetrazole rings and yield depends on the substrate, electronic effect of aryloxy group and reaction conditions. It was possible to introduce a thiomethoxymethyl group at 1 and 2-position of tetrazole via rearrangement of Swern intermediate.

Iminosulfuranes. XV. Dimethyl sulfoxide-trifluoroacetic anhydride. New and efficient reagent for the preparation of iminosulfuranes

1975 ◽  
Vol 40 (19) ◽  
pp. 2758-2764 ◽  
Author(s):  
Ashok K. Sharma ◽  
Thomas Ku ◽  
Arthur D. Dawson ◽  
Daniel Swern
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride ◽  
Efficient Reagent

Trifluoroacetic anhydride: A new activating agent for dimethyl sulfoxide in the synthesis of iminosulfuranes

1974 ◽  
Vol 15 (16) ◽  
pp. 1503-1506 ◽  
Author(s):  
Ashok K. Sharma ◽  
Daniel Swern
Keyword(s):  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Anhydride ◽  
Activating Agent
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