Reaction of olefins with nitriles under solvent-free conditions using molecular iodine as a catalyst in the presence of water

Journal of Oleo Science

Volumn 61, Issue 12, 2012, Pages 715-721

  Hanzawa, Yohko ^a   Kasashima, Yoshio ^a   Tomono, Kazuki ^b   Mino, Takashi ^b   Sakamoto, Masami ^b   Fujita, Tsutomu ^b  

^a CHIBA INSTITUTE OF TECHNOLOGY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Camphene; Iodine; Ritter reaction; Solvent free

Indexed keywords

ALIPHATIC NITRILES; AMIDATION; BENZAMIDES; BENZONITRILES; CAMPHENE; COMPLEX REACTIONS; CYCLOHEXENES; CYCLOOLEFINS; CYCLOPENTENES; HETEROCYCLIC COMPOUND; MOLAR RATIO; MOLECULAR IODINE; OPTIMIZED CONDITIONS; PRESENCE OF WATER; RITTER REACTIONS; SOLVENT FREE; SOLVENT FREE CONDITIONS;

AMIDES; AROMATIC COMPOUNDS; CATALYSTS; CYANIDES; IODINE; OLEFINS; SOLVENTS; STYRENE;

IODINE COMPOUNDS;

ALKENE; IODINE; NITRILE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; IODINE; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM; WATER;

EID: 84870878557     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.61.715     Document Type: Article

References (12)

1. Ritter, J. J.; Minieri, P. P. A New Reaction of Nitriles. I. Amides from Alkenes and Mononitriles. J. Am. Chem. Soc. 70, 4045-4048 (1948).
2. Clarke, T.; Devine, J.; Dicker, D. W. Application of the Ritter Reaction to α-Olefins. J. Am. Oil Chem. Soc. 41, 78-82 (1964).
3. Larock, R. C.; Leong, W. W. Comprehensive Organic Synthesis. (Trost, B. M.; Semmelhack, M. F. ed.) Vol. 4, Pergamon Press, Oxford, pp. 292-295 (1991).
4. Barbero, M.; Bazzi, S.; Cadamuro, S.; Dughera, S. Benzenedisulfonimide as a Reusable BrØnsted Acid Catalyst for Ritter-Type reactions. Eur. J. Org. Chem. 430-436 (2009).
5. Abe, T.; Takada, H.; Miwa, Y.; Yamada, K.; Ishikura, M. Copper-Catalyzed Ritter-Type Reaction of Unactivated Alkenes with Dichloramine-T. Helv. Chim. Acta 93, 233-241 (2010).
6. Reddy, K. L. An efficient method for the conversion of aromatic and aliphatic nitriles to the corresponding Ntert-butyl amides: a modified Ritter reaction. Tetrahedron Lett. 44, 1453-1455 (2003).
7. Kasashima, Y.; Uzawa, A.; Hashimoto, K.; Yokoyama, Y.; Mino, T.; Sakamoto, M.; Fujita, T. Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst. J. Oleo Sci., 59, 607-613 (2010).
8. Hanzawa, Y.; Kasashima, Y.; Tomono, K.; Mino, T.; Sakamoto, M.; Fujita, T. Synthesis of Amides Derived from Esters with Nitlies under Solvent-free Conditions Using Molecular Iodine as a Catalyst. J. Oleo Sci., in press.
9. Ren, Y.; Cai, C. A sovent-free synthesis of 1,2,4,5-tetrasubstituted imidazoles using molecular iodine as catalyst. J. Chem. Res. 34, 133-134 (2010).
10. Ide, Y.; Hori, Y.; Kobayashi, S.; Hossain, M. D.; Kitamura, T. A simple and convenient per-o-acylation of cyclodextrin catalyzed by molecular iodine. Synthesis, 18, 3083-3086 (2010).
11. Nizam, A.; Pasha, M. A. Iodine-catalyzed, rapid and efficient, one-pot synthesis of 1,2-dihydro-1-arylnaphtho-[1,2e] [1,3] oxazine-3-ones under solvent-free conditions. Synthetic Commun., 40, 2864-2868 (2010).
12. Madhusudana Reddy. M. B., Pasha, M. A. Iodine-catalyzed versatile synthesis of 4,6-siarlypyrimidin-2 (1H)-ones (DAPMs) via one-pot, multicomponent reacton. Synthetic Commun., 41, 1875-1880 (2011).