Metal carbonyls catalysed reaction of isocyanates with aldehydes

[en] A novel transition metal-catalysed reaction of isocyanates with aldehydes has been investigated. The reaction is of potential practical interest for the preparation of imines when water-sensitive groups are present. Kinetics and isotope labelling experiments indicate a rather complex mechanism; this implies a determinant insertion of the aldehyde into a preformed isocyanate complex, this true catalytic species being slowly produced through competitive coordination between the two reagents. The mechanism of similar catalysed reactions is discussed in the light of our own results. © 1981.

Disciplines :

Chemistry

Author, co-author :

Drapier, J.; Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liège, Sart Tilman, 4000 Liège, Belgium

Hoornaerts, M. T.; Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liège, Sart Tilman, 4000 Liège, Belgium

Hubert, André J.

Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Language :

English

Title :

Metal carbonyls catalysed reaction of isocyanates with aldehydes

Publication date :

1981

Journal title :

Journal of Molecular Catalysis

ISSN :

0304-5102

Publisher :

Elsevier, Netherlands

Volume :

Issue :

Pages :

53-68

Peer reviewed :

Peer reviewed

Available on ORBi :

since 29 May 2019

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Bibliography

Drapier, Hubert, Teyssie (1972) Reaction between aldehydes and isocyanates catalysed by metal carbonyls. Journal of the Chemical Society, Chemical Communications 484.
Drapier, Hubert, Teyssie Tetrahedron Lett. 1973, 419.
Drapier, Hubert, Teyssie (1975) Metal-Carbonyl Activation of Isocyanates; III. A One-Step Synthesis of Trisubstituted Dioxo-1,2,4-triazolidines, and a Direct Preparation ofN-Sulfenylaniline. Synthesis 649.
Ohao, Tsuji Chem. Commun. 1971, 247.
Ulrich, Tucker, Sayigh Tetrahedron Lett. 1967, 1731.
Ojima, Inaba Tetrahedron Lett. 1973, 4263.
Manuel Inorg. Chem. 1964, 3:1703.
Cenini, La Monica Inorg. Chim. Acta 1976, 18:279.
Lappert, Prokai Adv. Organomet. Chem. 1967, 5:225.
Kolomnikov, Lobeeva, Fulova, Vol'Pin Izv. Akad. Nauk. SSSR, Ser. Khim. 1973, 1379.
Mehrotra, Rai, Bohra J. Inorg. Nucl. Chem. 1974, 36:1887.
Noltes, Janssen J. Organomet. Chem. 1964, 1:346.
King, Bisnette Inorg. Chem. 1966, 5:306.
Kolomnikov, Koreshkov, Lobeeva, Vol'Pin Izv. Akad. Nauk. ASSR, Ser. Khim. 1972, 1181.
Collman, Kubota, Sun, Vastine J. Am. Chem. Soc. 1967, 89:169.
Collman, Kubota, Vastine, Sun, Kang J. Am. Chem. Soc. 1968, 90:5430.
Baird, Wilkinson (1967) Carbon disulphide, carbonyl sulphide, and alkyl and aryl isothiocyanate and perfluorothioacetone complexes of nickel, palladium, platinum, rhodium, and iridium. Journal of the Chemical Society A: Inorganic, Physical, Theoretical 865.
Hasegawa, Itoh, Ishii Inorganic Chemistry 1974, 13:2674.
Beck, Rieber, Cenini, Porta, La Monica (1974) Reactions of toluene-p-sulphonyl azide and isocyanate with low valent transition-metal complexes. Journal of the Chemical Society, Dalton Transactions 298.
Cenini, Pizzoti, Porta, La Monica J. Organomet. Chem. 1975, 88:237.
Dekker, Knox Chem. Commun. 1967, 1243.
Sappa, Milone J. Organomet. Chem. 1973, 61:383.
Graf (1968) Neuere Methoden der präparativen organischen Chemie VI Umsetzungen mitN-Carbonyl-sulfamidsäurechlorid. Angewandte Chemie 80:179.
Ulrich Chem. Rev. 1965, 65:369.
Knoppova, Komanova, Kada, Jurasek, Kovac (1974) Reactions of aromatic isothiocyanates with benzaldehydes. Collection of Czechoslovak Chemical Communications 39:3728.
Niwa, Aoki, Tanaka, Munakata, Namiki (1966) Notiz über eine neue Reaktion von Phenylisocyanat mit tertiären aromatischen Aldehyden. Chemische Berichte 99:3932.
D'Alelio, Crivello, Schoenig, Huemmer (1987) Polymeric Schiff Bases. II. The Synthesis of Azomethines by a Continuous Azeotropic Method. Journal of Macromolecular Science: Part A - Chemistry 1 A(7):1251.
Jungers, Sajus, de Aguirre, Decroocq L'Analyse Cinétique de la Transformation Chimique, Editions Technip 1968, 1123.
Cohen, Song J. Am. Chem. Soc. 1965, 87:3780.
Benson (1971) ALDEHYDES FROM ACID CHLORIDES BY MODIFIED ROSENMUND REDUCTION: 3,4,5-TRIMETHOXYBENZALDEHYDE. Organic Syntheses 51:8.
Rose, Statnam (1950) 16. Acetylene reactions. Part VI. Trimerisation of ethynyl compounds. Journal of the Chemical Society (Resumed) 69.
Hieber, Pigenot (1956) Über Metallcarbonyle, 70. Mitteil.: Isonitril-substituierte Eisencarbonyle. Chemische Berichte 89:193.
Zweifel, Brown Org. React. 1963, 13:28.
Ferguson, Branch J. Am. Chem. Soc. 1944, 66:1467.
Smith Tetrahedron 1963, 19:445.
Huhn, Mansal, Markovic, Vargazon Arch. Kem. 1954, 26:21.
Freund, Becker Ber. 1903, 36:1538.
Roe, Montgomery J. Am. Chem. Soc. 1953, 75:910.
Law J. Chem. Soc. 1912, 101:154.
Tabei, Sailou (1969) The Nuclear Magnetic Resonance and Infrared Spectra of Aromatic Azomethines. Bulletin of the Chemical Society of Japan 42:1440.
Clougherty, Sousa, Wyman Org. Chem. 1957, 22:462.
Ebara (1961) Benzylideneaniline. III. Anils of Substituted Benzaldehydes. Bulletin of the Chemical Society of Japan 34:1151.
Cossu-Jouve, Savon, Ucciani Bull. Soc. Chim. Fr. 1973, 2429.
Monagle, Campbell, Mc Sinane J. Am. Chem. Soc. 1962, 84:4288.
Hine Physical Organic Chemistry (Second) Edition, International Student Edition 1962, 87.
Wilkins The Study of Kinetics and Mechanism of Reactions of Transition Metal Complexes , Allyn and Bacon; 1974, 80.
Baini, Nyman, Wilkinson J. Chem. Soc. (A) 1968, 348.
Suszend, Weber (1970) Etude de compos�s d'addition des acides deLewis - XXXI [1]. Compos�s d'addition de divers ald�hydes aliphatiques et aromatiques. Helvetica Chimica Acta 53:2085.
Ohshiro, Kinugasa, Minami, Agawa J. Org. Chem. 1970, 35:2136.
Collman, Roper Adv. Organomet. Chem. 1968, 7:54.
Cotton, Zingales J. Am. Chem. Soc. 1961, 83:351.
Cotton, Parish (1960) 290. The stereochemistry of five-co-ordinate compounds. Part I. Infrared spectra of some iron(0) compounds. Journal of the Chemical Society (Resumed) 1440.
.
Knifton J. Org. Chem. 1973, 38:3296.
Dowd, Kang (1974) Stereospecific deoxygenation of epoxides with octacarbonyldicobalt. Journal of the Chemical Society, Chemical Communications 384.