RSS-Feed abonnieren
DOI: 10.1055/s-2003-36779
Organic Reactions in Water: Highly Rapid CAN Mediated One-Pot Synthesis of Nitriles from Aldehydes under Mild Conditions
Publikationsverlauf
Publikationsdatum:
22. Januar 2003 (online)
![](https://www.thieme-connect.de/media/synlett/200302/lookinside/thumbnails/10.1055-s-2003-36779-1.jpg)
Abstract
A variety of aliphatic and aromatic nitriles were prepared from the corresponding aldehydes in high yield in a direct one pot and rapid process using ceric ammonium nitrate (CAN) in amonia-water under mild conditions.
Key words
ceric ammonium nitrate (CAN) - aldehydes - nitriles - organic reactions in water
-
1a
Mowry DT. Chem. Rev. 1948, 42: 250 -
1b
Friedrich K.Wallensfels K. In The Chemistry of the Cyano GroupRappoport Z. Wiley-Intersicnece; New York: 1970. -
1c
North M. In Comprehensive Organic Functional Group TransformationKatrizky AR.Meth-Cohn O.Rees CW. Pergamon; Oxford: 1995. p.617-618 -
2a
Findlay JA.Tang CS. Can. J. Chem. 1967, 45: 1014 -
2b
Forey HG.Datlon DR. J. Chem. Soc., Chem. Commun. 1973, 628 -
2c
Kukhar VP.Fasternak VI. Synthesis 1974, 563 -
2d
Shinozaki H.Imaizumi M.Tajima M. Chem. Lett. 1983, 929 -
2e
Meshram HM. Synthesis 1992, 943 -
2f
Katritzky AR.Zhang GF.Fan WQ. Org. Prep. Proced. Int. 1993, 25: 315 -
2g
Krause JG.Shaikh S. Synthesis 1974, 563 -
2h
Flukuzaiwa S.Yamaishi Y.Funiya H.Terao K.Iwasaki F. Tetrahedron Lett. 1997, 38: 7203 -
2i
Villemin D.Lalaoui M.Ben Alloum A. Chem. Ind. (London) 1991, 176 -
2j
Rosini G.Baccolini G.Cacchi S. J. Org. Chem. 1973, 38: 1060 -
2k
Olah GA.Narang SC.Garcia-Luna A. Synthesis 1980, 659 -
2l
Olah GA.Vankar YD.Garcia-Luna A. Synthesis 1979, 227 -
3a
Blatter HM.Lukaszewski H.de Stevens G. J. Am. Chem. Soc. 1961, 83: 2203 -
3b
Olah GA.Keumi T. Synthesis 1979, 112 ; and references cited therein -
3c
Daunzonne D.Demerseman P.Royer R. Synthesis 1981, 739 -
3d
Saednya A. Synthesis 1982, 190 -
3e
Ganboa I.Palomo C. Synth. Commun. 1983, 13: 219 -
3f
Capeceivelle P.Lavigne A.Maumy M. Synthesis 1989, -
3g
Bose DS.Narsaiah AV. Tetrahedron Lett. 1998, 39: 6533 -
3h
Karmarkar SN.Kelkar SL.Wadia MS. Synthesis 1985, 510 -
3i
Dauzonne D.Demergeman P.Royer R. Synthesis 1981, 739 -
3j
Dauzonne D.Demerseman P.Royer R. Synthesis 1981, 739 -
3k
Miller M.Loudon G. J. Org. Chem. 1975, 40: 126 -
3l
Fizet C.Streith . J. Org. Chem. 1975, 40: 126 -
3m
Sosnovsky G.Krogh JA.Umhoefer SG. Synthesis 1979, 722 -
3n
Olah GA.Keuni T. Synthesis 1979, 112 -
4a
Pomeroy JH.Craig CA. J. Am. Chem. Soc. 1959, 81: 6340 -
4b
Gela-Mialhe Y.Vessiere R. Synthesis 1980, 1005 -
4c
Furukawa N.Fukumura M.Akasaka T.Yoshimura T.Oae S. Tetrahedron Lett. 1980, 21: 761 -
4d
Georg GI.Pfeifer SA. Tetrahedron Lett. 1985, 26: 2739 -
4e
Nishiyama K.Oba M.Watanabe A. Tetrahedron 1987, 43: 693 -
4f
Suzuki H.Nakaya C. Synthesis 1992, 641 -
5a
Villemin D.Lalaoui M.Alloum AB. Chem. Ind. (London) 1991, 176 -
5b
Delgado E.Cano AC.Garcia O.Alvarado J.Velasco L.Alvarez C.Rudler H. Synth. Commun. 1992, 2125 -
5c
Feng JC.Lin Ba L.Bian NS. Synth. Commun. 1998, 28: 3765 -
5d
Das B.Madhusudhan P.Venkataiah B. Synlett 1999, 1569 - 6
Brackman W.Smit P. J. Recl. Trev. Chim. 1963, 82: 757 - 7
Parameswaran KN.Friedman OM. Chem. Ind. (London) 1965, 988 - 8
Misono A.Osa T.Koda S. Bull. Chem. Soc. Jpn. 1966, 39: 854 - 9
Sato R.Itoh Y.Itep K.Ni hina H.Goto T.Saito M. Chem. Lett. 1984, 1913 - 10
Okimoto M.Chiba T. J. Org. Chem. 1978, 5: 218 - 11
Erman MB.Snow JW.Williams MJ. Tetrahedron Lett. 2000, 41: 6749 - 12
Talukdar S.Hsu JL.Chou TC.Fang JM. Tetrahedron Lett. 2001, 42: 1103 - 13
Roesky HW.Mockel K. Chemical Curiosities VCH; Weinhein: 1996. p.292-293
References
(14)(3,4,5-Triacetoxy)pentanenitrile (15): [α]D 25 7.3 (c 2.6, CHCl3). IR (neat): 2265cm-1. 1H NMR (300 MHz, CDCl3): δ = 2.1 (s, 3 H, COCH3), 2.15 (s, 3 H, COCH3), 2.18 (s, 3 H, COCH3), 2.6-2.7 (m, 2 H, CH2CN), 4.15 (dd, J = 12.2 and 4.5 Hz, 1 H), 4.35 (dd, J = 12.2 and 3.3 Hz, 1 H), 5.2-5.3 (m, 2 H, CH2O). 13C NMR (75 MHz, CDCl3): δ = 17 (CH2), 21 (2 × CH3), 22.5 (CH3), 62.3(CH2), 65.7 (CH), 72.1 (CH), 123.2 (C), 171.4 (C), 171.8 (C), 172.1 (C). Anal. Calcd for C11H15O6N (257.24): C, 51.36; H, 5.88; N, 5, 45. Found: C, 51.41; H, 5.71; N, 5.49.