Abstract
Dimethyl dithiocarbonate (DMDTC) has been shown to be an efficient dehydrating agent for a range of oximes derived from aliphatic, aromatic and heteroaromatic aldehydes yielding the corresponding nitriles in high yields.
Key words
DMDTC - nitriles - oximes - dehydration
References
1a North M. In Comprehensive Organic Functional Group Transformations
Katritzky AR.
Meth-Cohn O.
Rees CW.
Pergamon;
Oxford:
1995.
p.617-618
1b Tennant G. In Comprehensive Organic Chemistry
Vol. 2:
Barton DHR.
Ollis WD.
Pergamon;
Oxford:
1979.
Chap. 8.
p.534-535
1c Luo F.-T.
Jeevanandam A.
Tetrahedron Lett.
1998,
39:
9455
1d Yamada H.
Chimia
1993,
47:
69
1e Crossby J.
Moiller J.
Parratt JS.
Turner NJ.
J. Chem. Soc., Perkin Trans. 1
1994,
1679
1f Cohen MA.
Sawden J.
Turner NJ.
Tetrahedron Lett.
1990,
31:
7223
2a Friedrich K.
Wallensfels K. In The Chemistry of the Cyano Group
Rappaport Z.
Wiley-Interscience;
New York:
1970.
p.67
2b Fatiadi AJ. In Preparation and Synthetic Application of Cyano Compounds
Patai S.
Rappaport Z.
Wiley;
New York:
1983.
p.1057
2c Miller JS.
Manson JL.
Acc. Chem. Res.
2001,
34:
563
2d Wang E.-C.
Lin G.-J.
Tetrahedron Lett.
1998,
39:
4047
2e Medwid JB.
Paul R.
Baker JS.
Brockman JA.
Du MT.
Hallett WA.
Hanifin JW.
Hardy RA.
Tarrant ME.
Torley LW.
Wrenn S.
J. Med. Chem.
1990,
33:
1230
2f Judkins BD.
Allen DG.
Cook TA.
Evans B.
Sardharwala TE.
Synth. Commun.
1996,
26:
4351
3a Katritzky AR.
Zhang GF.
Fan WQ.
Org. Prep. Proced. Int.
1993,
25:
315
3b Larock RC.
Comprehensive Organic Transformations
VCH;
New York:
1989.
3c Ishihara K.
Furuya Y.
Yamamoto H.
Angew. Chem. Int. Ed.
2002,
41:
2983
3d Choi E.
Lee C.
Na Y.
Chang S.
Org. Lett.
2002,
4:
2369
3e Yang SH.
Chang S.
Org. Lett.
2001,
3:
4209 ; and references therein
3f Sharghi H.
Sarvari MH.
Synthesis
2003,
243
3g Sharghi H.
Sarvari MH.
Tetrahedron
2002,
58:
10323
3h Bandgar BP.
Makone SS.
Synlett
2003,
262
3i Boruah M.
Konwar D.
J. Org. Chem.
2002,
67:
7138
3j DeLuca L.
Giacomelli G.
Porcheddu A.
J. Org. Chem.
2002,
67:
6272
3k Fukuzawa S.-i..
Yamaishi Y.
Furuya H.
Terao K.
Iwasaki F.
Tetrahedron Lett.
1997,
38:
7203
3l Meshram HM.
Synthesis
1992,
943
3m Villemin D.
Lalaoni M.
Ben Alloum A.
Chem. Ind. (London)
1991,
176
3n Hendrickson JB.
Hussoin MS.
J. Org. Chem.
1987,
52:
4137
3o Molina P.
Alajarib M.
Vilaplana MJ.
Synthesis
1982,
1016
3p Olah GA.
Narang S.
Garcia-Luna A.
Synthesis
1980,
659
3q Olah GA.
Vankar YD.
Garcia-Luna A.
Synthesis
1979,
227
3r Kukhar VP.
Pastlernak VI.
Synthesis
1974,
563
3s Foley HG.
Dalton DR.
J. Chem. Soc., Chem. Commun.
1973,
628
4 Prokipcak JM.
Forte PA.
Can. J. Chem.
1971,
49:
1321
5 Ila H.
Junjappa H.
Mahanta PK. In Progress in Heterocyclic Chemistry
Vol. 13:
Gilchrist TL.
Gribble G.
Pergamon;
New York:
2001.
Chap. 1.
p.1
6 Dhar S.
Mohanta PK.
Ila H.
Junjappa H.
Tetrahedron
2000,
56:
629
7 Leung M.-K.
Lai J.-L.
Lau K.-L.
Vu H.-H.
Hsiao H.-J.
J. Org. Chem.
1996,
61:
4175
8 Kawata T.
Harano K.
Taguchi T.
Chem. Pharm. Bull.
1973,
21:
604
9a Nakayama Y.
Senokuchi K.
Sakaki K.
Kato M.
Maruyama T.
Miyazaki T.
Ito H.
Nakai H.
Kawamura M.
Bioorg. Med. Chem.
1997,
5:
971
9b Suzuki S.
Fujita Y.
Nishida T.
Synth. Commun.
1984,
14:
817
10 All nitriles were characterized by comparison of their physical and spectroscopic data with reported data.
11
General Procedure for Preparation of Nitriles : To a solution of the appropriate oxime 2 (1 mmol), DMDTC (0.14 g, 1.1 mmol) and Et3 N (0.70 mL, 5.0 mmol) in dioxane (15 mL) were heated with stirring at 90 °C for 8-11 h (monitored by TLC). Concentration under reduced pressure gave crude product, which was filtered through a short silica gel column using hexane-EtOAc as eluent to give the corresponding nitrile 4 .
