Derivatives of orthoacids. IV. Acid-catalysed thermal eliminations and baseinduced eliminations of some 2-Ethoxy-1,3-dioxolans

1968 ◽  
Vol 21 (8) ◽  
pp. 2013 ◽  
Author(s):  
JS Josan ◽  
FW Eastwood

A series of phenyl substituted 2-ethoxy-1,3-dioxolans (orthoformates) has been prepared and their stereochemistry assigned. When heated in the presence of a carboxylic acid they underwent a stereospecific cis elimination to form the corresponding olefins, carbon dioxide, and ethanol. Provided that one 4 or 5 position in these dioxolans was unsubstituted, they reacted with butyllithium through elimination of the elements of ethyl formate and the formation of a carbonyl compound. The eliminated portion was always converted by the butyllithium into nonan-5-ol. A simple preparative method for cis-stilbene is described.

1964 ◽  
Vol 17 (12) ◽  
pp. 1392 ◽  
Author(s):  
G Crank ◽  
FW Eastwood

Ethyl orthoformate reacted with pinacol to form 2-ethoxy-4,4,5,5-tetramethyl-1,3-dioxolan (I) which decomposed on heating to yield ethanol, carbon dioxide, and 2,3-dimethylbut-2-ene. When subjected to the same reaction sequence diethyl- D-tartrate, diethyl-meso-tartrate, meso-1,2-diphenylethane-1,2-diol, and cis-cyclo-hexane-1,2-dial underwent specific cis-elimination to yield diethyl fumarate, diethyl maleate, cis-stilbene, and cyclohexane respectively. Glycerol, butane-1,2,4-trial, and pentane-1,2,5-triol formed polymers which decomposed to yield allyl alcohol, but-1-en-4-ol, and pent-1-en-5-ol respectively. Pyrolysis of the monoformyl esters of cis-cyclohexane-1,2-diol, glycerol, butane-1,2,4-triol, and pentane-l,2,5-trio1 gave the respective products enumerated above whereas the monoformyl ester of pinacol yielded pinacolone. When compound (I) was heated in the presence of p-toluenesulphonic acid it gave ethyl formate, pinacolone, 2,3-dimethylbutadiene, and water.


2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.


2009 ◽  
Vol 66 (4) ◽  
pp. 417-424 ◽  
Author(s):  
Greg Dojchinov ◽  
Katherine A Damcevski ◽  
James D Woodman ◽  
Victoria S Haritos

1960 ◽  
Vol 2 (3) ◽  
pp. 263-269 ◽  
Author(s):  
Paolo Da Re ◽  
Lucia Verlicchi ◽  
Ivo Setnikar

Molecules ◽  
2006 ◽  
Vol 11 (12) ◽  
pp. 968-977 ◽  
Author(s):  
Mario Sechi ◽  
Fabio Casu ◽  
Ilaria Campesi ◽  
Stefano Fiori ◽  
Alberto Mariani

Heterocycles ◽  
1997 ◽  
Vol 45 (4) ◽  
pp. 787 ◽  
Author(s):  
Yvette A. Jackson ◽  
Mark F. Williams

1984 ◽  
Vol 21 (3) ◽  
pp. 681-683 ◽  
Author(s):  
Raymond Houssin ◽  
Jean-Luc Bernier ◽  
Jean-Pierre Hénichart

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