Triphenylphosphine-iodine: An efficient reagent system for the synthesis of nitriles from aldoximes

Synthetic Communications

Volumn 36, Issue 2, 2006, Pages 137-140

  Venkat Narsaiah, A ^a   Sreenu, D ^a   Nagaiah, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldoximes; Dehydration; Iodine; Nitriles; Triphenlyphosphine

Indexed keywords

ALDOXIME; IODINE; NITRILE; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL REACTION; HYDRATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 31144467620     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500333225     Document Type: Article

References (13)

1. (a) Sharghi, H.; Sarvari, M. H. A direct synthesis of nitriles and amides from aldehydes using dry or wet alumina in solvent-free conditions. Tetrahedron 2002, 58, 10323-10328;
2. (b) Bose, D. S.; Narsaiah, A. V. Efficient one-pot synthesis of nitriles from aldehydes in solid state using peroxymonosulfate on alumina. Tetrahedron Lett. 1998, 39, 6533-6534;
3. 3CN: A new alternate system for dehydration of oximes and amides in hydrated media. J. Org. Chem. 2002, 67, 7138-7139.
4. (a) Ishihara, K.; Furuya, Y.; Yamamoto, H. Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles. Angew. Chem. Int., Ed. Engl. 2002, 41, 2983-2986;
5. (b) Narsaiah, A. V.; Nagaiah, K. An efficient and improved method for the preparation of nitriles from primary amides and aldoximes. Adv. Synth. Cat. 2004, 346, 1271-1274;
6. (c) Bose, D. S.; Narsaiah, A. V. Use of PyBOP as a convenient activator for the synthesis of nitriles from primary amides. Synthesis 2001, 3, 373-375;
7. (d) Heck, M. P.; Wagner, A.; Mioskowski, C. Conversion of primary amides to nitriles by aldehydes-catalyzed water transfer. J. Org. Chem. 1996, 61, 6486-6487;
8. (e) Fukuzawa, S.; Yamaishi, Y.; Furuya, H.; Terao, K.; Iwasaki, F. Effective transformation of aldoximes to nitriles by dehydration with 2-methylene-1,3-dioxepane in the presence of a Lewis acid catalyst. Tetrahedron Lett. 1997, 38, 7203-7206;
9. (f) Yang, S. H.; Chang, S. Highly efficient and catalytic conversion of aldoximes to nitriles. Org. Lett. 2001, 3, 4209-4211.
10. (a) Narsaiah, A. V.; Basak, A. K.; Nagaiah, K. Cadmium chloride: An efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2-[1H]-ones. Synthesis 2004, 8, 1253-1256;
11. (b) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K. Phosphane-catalyzed Knoevenagel condensation: A facile synthesis of α-cyanoacrylates and α-cyanoacrylonitriles. Eur. J. Org. Chem. 2004, 546-551;
12. 3: An ecofriendly system for synthesis of diaryl ethers under microwave irradiation. Ind. J. Chem., Sect. B 2004, 11, 2478-2481;
13. (d) Narsaiah, A. V.; Nagaiah, K. Antimony pentachloride-promoted regeneration of carbonyl compounds from oximes. Synthesis 2003, 12, 1881-1882.