The reaction was named after Karl Wilhelm Rosenmund who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of potassium cyanide and catalytic amounts of cuprous cyanide at 200 °C. The reaction yields the carboxylic acid, not the nitrile, but Rosenmund speculated that the intermediate should be the nitrile.[1] Independently Alfred Pongratz[4] and Julius von Braun [de][2] improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction. Further improvement of the reaction was done in the following years,[5] for example the use of ionic liquids as solvent for the reaction.[6]
^ abRosenmund, Karl W.; Struck, Erich (27 September 1919). "Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 52 (8): 1749–1756. doi:10.1002/cber.19190520840.
^ abv. Braun, Julius; Manz, Gottfried (1931). "Fluoranthen und seine Derivate. III. Mitteilung". Justus Liebig's Annalen der Chemie. 488 (1): 111–126. doi:10.1002/jlac.19314880107.
^E. Callen, Joseph; A. Dornfeld, Clinton; H. Coleman, George (1948). "9-CYANOPHENANTHRENE". Organic Syntheses. 28 (28): 34. doi:10.15227/orgsyn.028.0034.
^Pongratz, Alfred (July 1927). "Untersuchungen über Perylen und seine Derivate". Monatshefte für Chemie. 48 (7): 585–591. doi:10.1007/BF01518076. S2CID 197767053.
^KOELSCH, C. F.; WHITNEY, A. G. (November 1941). "THE ROSENMUND-von BRAUN NITRILE SYNTHESIS". The Journal of Organic Chemistry. 06 (6): 795–803. doi:10.1021/jo01206a002.
^Wu, Jeff Xin; Beck, Brandon; Ren, Rex X. (January 2002). "Catalytic Rosenmund–von Braun reaction in halide-based ionic liquids". Tetrahedron Letters. 43 (3): 387–389. doi:10.1016/S0040-4039(01)02168-2.
January 07, 2023
rosenmund, braun, reaction, rosenmund, braun, synthesis, organic, reaction, which, aryl, halide, reacts, with, cuprous, cyanide, yield, aryl, nitrile, rosenmund, braun, reactionnamed, after, karl, wilhelm, rosenmund, julius, braunreaction, type, substitution, . The Rosenmund von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to yield an aryl nitrile 1 2 3 Rosenmund von Braun reactionNamed after Karl Wilhelm Rosenmund Julius von BraunReaction type Substitution reactionIdentifiersOrganic Chemistry Portal rosenmund von braun reactionRSC ontology ID RXNO 0000288 The reaction was named after Karl Wilhelm Rosenmund who together with his Ph D student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of potassium cyanide and catalytic amounts of cuprous cyanide at 200 C The reaction yields the carboxylic acid not the nitrile but Rosenmund speculated that the intermediate should be the nitrile 1 Independently Alfred Pongratz 4 and Julius von Braun de 2 improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction Further improvement of the reaction was done in the following years 5 for example the use of ionic liquids as solvent for the reaction 6 Other exampleSee also EditKolbe nitrile synthesis a similar reaction for the synthesis of alkyl nitrile Sandmeyer reaction Von Braun reactionReferences Edit a b Rosenmund Karl W Struck Erich 27 September 1919 Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten I Mitteilung Ersatz des Halogens durch die Carboxylgruppe Berichte der Deutschen Chemischen Gesellschaft A and B Series 52 8 1749 1756 doi 10 1002 cber 19190520840 a b v Braun Julius Manz Gottfried 1931 Fluoranthen und seine Derivate III Mitteilung Justus Liebig s Annalen der Chemie 488 1 111 126 doi 10 1002 jlac 19314880107 E Callen Joseph A Dornfeld Clinton H Coleman George 1948 9 CYANOPHENANTHRENE Organic Syntheses 28 28 34 doi 10 15227 orgsyn 028 0034 Pongratz Alfred July 1927 Untersuchungen uber Perylen und seine Derivate Monatshefte fur Chemie 48 7 585 591 doi 10 1007 BF01518076 S2CID 197767053 KOELSCH C F WHITNEY A G November 1941 THE ROSENMUND von BRAUN NITRILE SYNTHESIS The Journal of Organic Chemistry 06 6 795 803 doi 10 1021 jo01206a002 Wu Jeff Xin Beck Brandon Ren Rex X January 2002 Catalytic Rosenmund von Braun reaction in halide based ionic liquids Tetrahedron Letters 43 3 387 389 doi 10 1016 S0040 4039 01 02168 2 Retrieved from https en wikipedia org w index php title Rosenmund von Braun reaction amp oldid 1094585399, wikipedia, wiki, book, books, library,
