The Ritter Reaction in Liquid Sulfur Dioxide
Material Science and Applied Chemistry: Scientific Journal of Riga Technical University. 2015
Daniels Posevins

Ritter reaction is associated with a one-pot process for amide bond formation, that involves nitrile and a group, capable of giving a relatively stable carbenium ion (originally - alcohol or alkene) in strongly ionizing acidic medium. The classical Ritter reaction involves use of at least stoichiometric amounts of a corrosive Brønsted acid (i.e., conc. H2SO4), thus often limiting its applicability to compounds containing acid labile functional groups. Nevertheless because of its atom economy and easy application Ritter reaction proved to be useful in synthesis of different biological molecules and pharmaceuticals. Over past two decades a huge progress has been made in development of catalytic variations of the Ritter reaction. SO2 is a colorless, non-combustible gas, that makes up about one part per billion (ppb) by volume in atmosphere. It has also found its application as a food preservative, for example, as an antioxidant and anti-microbial in wine manufacture. Gaseous SO2 can be easily liquefied to give a colorless, mobile liquid (SO2(liq.)) with relatively low vapor pressure (about 3 bar at 20 oC), that can be used as a commercially acceptable solvent or reagent for synthetic chemistry preparations. Unique characteristics of SO2(liq.) as a reaction medium has previously been observed by P. Walden and G. A. Olah. One of such properties that was found particularly attractive is the ability to facilitate formation of carbenium ions. Having regard of the aforementioned unique properties of SO2(liq.) as a solvent reported we became interested in possible application of SO2(liq.) as a solvent for the Ritter reaction. To the best of our knowledge the sole example of the Ritter reaction that was carried out in SO2(liq.) refers to work of Bakke and Knudsen, who studied dicyclopentadiene-derived carbenium ion rearrangements during the Ritter reaction and concluded that in SO2(liq.) the reaction can be performed at lower temperature with well-defined configuration of resulting nitrile adduct.


Atslēgas vārdi
Amides, Ritter reaction, alcohols, nitriles

Posevins, D. The Ritter Reaction in Liquid Sulfur Dioxide. Materiālzinātne un lietišķā ķīmija . Nr.31, 2015, 60.-60.lpp. ISSN 1407-7353. e-ISSN 2255-8713.

Publikācijas valoda
English (en)
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