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
References
<A NAME="RD19702ST-1A">1a </A>
Mowry DT.
Chem. Rev.
1948,
42:
250
<A NAME="RD19702ST-1B">1b </A>
Friedrich K.
Wallensfels K. In The
Chemistry of the Cyano Group
Rappoport Z.
Wiley-Intersicnece;
New
York:
1970.
<A NAME="RD19702ST-1C">1c </A>
North M. In Comprehensive Organic Functional Group Transformation
Katrizky AR.
Meth-Cohn O.
Rees CW.
Pergamon;
Oxford:
1995.
p.617-618
<A NAME="RD19702ST-2A">2a </A>
Findlay JA.
Tang CS.
Can. J. Chem.
1967,
45:
1014
<A NAME="RD19702ST-2B">2b </A>
Forey HG.
Datlon DR.
J.
Chem. Soc., Chem. Commun.
1973,
628
<A NAME="RD19702ST-2C">2c </A>
Kukhar VP.
Fasternak VI.
Synthesis
1974,
563
<A NAME="RD19702ST-2D">2d </A>
Shinozaki H.
Imaizumi M.
Tajima M.
Chem.
Lett.
1983,
929
<A NAME="RD19702ST-2E">2e </A>
Meshram HM.
Synthesis
1992,
943
<A NAME="RD19702ST-2F">2f </A>
Katritzky AR.
Zhang GF.
Fan WQ.
Org. Prep. Proced. Int.
1993,
25:
315
<A NAME="RD19702ST-2G">2g </A>
Krause JG.
Shaikh S.
Synthesis
1974,
563
<A NAME="RD19702ST-2H">2h </A>
Flukuzaiwa S.
Yamaishi Y.
Funiya H.
Terao K.
Iwasaki F.
Tetrahedron
Lett.
1997,
38:
7203
<A NAME="RD19702ST-2I">2i </A>
Villemin D.
Lalaoui M.
Ben Alloum A.
Chem.
Ind. (London)
1991,
176
<A NAME="RD19702ST-2J">2j </A>
Rosini G.
Baccolini G.
Cacchi S.
J.
Org. Chem.
1973,
38:
1060
<A NAME="RD19702ST-2K">2k </A>
Olah GA.
Narang SC.
Garcia-Luna A.
Synthesis
1980,
659
<A NAME="RD19702ST-2L">2l </A>
Olah GA.
Vankar YD.
Garcia-Luna A.
Synthesis
1979,
227
<A NAME="RD19702ST-3A">3a </A>
Blatter HM.
Lukaszewski H.
de Stevens G.
J. Am. Chem. Soc.
1961,
83:
2203
<A NAME="RD19702ST-3B">3b </A>
Olah GA.
Keumi T.
Synthesis
1979,
112 ; and references cited therein
<A NAME="RD19702ST-3C">3c </A>
Daunzonne D.
Demerseman P.
Royer R.
Synthesis
1981,
739
<A NAME="RD19702ST-3D">3d </A>
Saednya A.
Synthesis
1982,
190
<A NAME="RD19702ST-3E">3e </A>
Ganboa I.
Palomo C.
Synth. Commun.
1983,
13:
219
<A NAME="RD19702ST-3F">3f </A>
Capeceivelle P.
Lavigne A.
Maumy M.
Synthesis
1989,
<A NAME="RD19702ST-3G">3g </A>
Bose DS.
Narsaiah AV.
Tetrahedron
Lett.
1998,
39:
6533
<A NAME="RD19702ST-3H">3h </A>
Karmarkar SN.
Kelkar SL.
Wadia MS.
Synthesis
1985,
510
<A NAME="RD19702ST-3I">3i </A>
Dauzonne D.
Demergeman P.
Royer R.
Synthesis
1981,
739
<A NAME="RD19702ST-3J">3j </A>
Dauzonne D.
Demerseman P.
Royer R.
Synthesis
1981,
739
<A NAME="RD19702ST-3K">3k </A>
Miller M.
Loudon G.
J. Org. Chem.
1975,
40:
126
<A NAME="RD19702ST-3L">3l </A>
Fizet C.
Streith .
J. Org. Chem.
1975,
40:
126
<A NAME="RD19702ST-3M">3m </A>
Sosnovsky G.
Krogh JA.
Umhoefer SG.
Synthesis
1979,
722
<A NAME="RD19702ST-3N">3n </A>
Olah GA.
Keuni T.
Synthesis
1979,
112
<A NAME="RD19702ST-4A">4a </A>
Pomeroy JH.
Craig CA.
J. Am. Chem. Soc.
1959,
81:
6340
<A NAME="RD19702ST-4B">4b </A>
Gela-Mialhe Y.
Vessiere R.
Synthesis
1980,
1005
<A NAME="RD19702ST-4C">4c </A>
Furukawa N.
Fukumura M.
Akasaka T.
Yoshimura T.
Oae S.
Tetrahedron
Lett.
1980,
21:
761
<A NAME="RD19702ST-4D">4d </A>
Georg GI.
Pfeifer SA.
Tetrahedron
Lett.
1985,
26:
2739
<A NAME="RD19702ST-4E">4e </A>
Nishiyama K.
Oba M.
Watanabe A.
Tetrahedron
1987,
43:
693
<A NAME="RD19702ST-4F">4f </A>
Suzuki H.
Nakaya C.
Synthesis
1992,
641
<A NAME="RD19702ST-5A">5a </A>
Villemin D.
Lalaoui M.
Alloum AB.
Chem. Ind. (London)
1991,
176
<A NAME="RD19702ST-5B">5b </A>
Delgado E.
Cano AC.
Garcia O.
Alvarado J.
Velasco L.
Alvarez C.
Rudler H.
Synth. Commun.
1992,
2125
<A NAME="RD19702ST-5C">5c </A>
Feng JC.
Lin Ba L.
Bian NS.
Synth. Commun.
1998,
28:
3765
<A NAME="RD19702ST-5D">5d </A>
Das B.
Madhusudhan P.
Venkataiah B.
Synlett
1999,
1569
<A NAME="RD19702ST-6">6 </A>
Brackman W.
Smit P.
J. Recl. Trev. Chim.
1963,
82:
757
<A NAME="RD19702ST-7">7 </A>
Parameswaran KN.
Friedman OM.
Chem. Ind. (London)
1965,
988
<A NAME="RD19702ST-8">8 </A>
Misono A.
Osa T.
Koda S.
Bull.
Chem. Soc. Jpn.
1966,
39:
854
<A NAME="RD19702ST-9">9 </A>
Sato R.
Itoh Y.
Itep K.
Ni hina H.
Goto T.
Saito M.
Chem.
Lett.
1984,
1913
<A NAME="RD19702ST-10">10 </A>
Okimoto M.
Chiba T.
J. Org. Chem.
1978,
5:
218
<A NAME="RD19702ST-11">11 </A>
Erman MB.
Snow JW.
Williams MJ.
Tetrahedron Lett.
2000,
41:
6749
<A NAME="RD19702ST-12">12 </A>
Talukdar S.
Hsu JL.
Chou TC.
Fang JM.
Tetrahedron Lett.
2001,
42:
1103
<A NAME="RD19702ST-13">13 </A>
Roesky HW.
Mockel K.
Chemical
Curiosities
VCH;
Weinhein:
1996.
p.292-293
<A NAME="RD19702ST-14">14 </A>
(14)(3,4,5-Triacetoxy)pentanenitrile
(15) : [α]D
25 7.3
(c 2.6, CHCl3 ). IR (neat):
2265cm-1 . 1 H 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, CH2 CN),
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, CH2 O). 13 C
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 C11 H15 O6 N
(257.24): C, 51.36; H, 5.88; N, 5, 45. Found: C, 51.41; H, 5.71;
N, 5.49.