Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2005(9): 1456-1458
DOI: 10.1055/s-2005-868511
DOI: 10.1055/s-2005-868511
LETTER
© Georg Thieme Verlag Stuttgart · New York
Direct Oxidative Conversion of Primary Alcohols to Nitriles Using Molecular Iodine in Ammonia Water
Further Information
Received
23 March 2005
Publication Date:
29 April 2005 (online)
Publication History
Publication Date:
29 April 2005 (online)
Abstract
A simple, effective, high-yield procedure for the direct oxidative conversion of alcohols to nitriles, was successfully carried out with molecular iodine in ammonia water.
Key words
molecular iodine - oxidation - alcohol - nitrile - ammonia water
-
1a
Friedrick K.Wallensfels K. The Chemistry of the Cyano GroupRappoport Z. Wiley-Interscience; New York: 1970. -
1b
North M. Comprehensive Organic Functional Group TransformationsKatritzky AR.Meth-Cohn O.Rees CW. Pergamon; Oxford: 1995. -
2a
Wipf P. Chem. Rev. 1995, 95: 2115 -
2b
Wipf P.Yokokawa F. Tetrahedron Lett. 1998, 39: 2223 -
2c
Ducept PC.Marsden SP. Synlett 2000, 692 -
2d
Chihiro M.Nagamoto H.Takemura I.Kitano K.Komatsu H.Sekiguchi K.Tabusa F.Mori T.Tominaga M.Yabuuchi Y. J. Med. Chem. 1995, 38: 353 -
2e
Gu X.-H.Wan X.-Z.Jiang B. Bioorg. Med. Chem. Lett. 1999, 9: 569 -
2f
Kadaba PK. Synthesis 1973, 71 -
2g
Diana GD.Cutcliffe D.Volkots DL.Mallamo JP.Bailey TR.Vescio N.Oglesby RC.Nitz TJ.Wetzel J.Giranda V.Pevear DC.Dutko FJ. J. Med. Chem. 1993, 36: 3240 -
2h
Wittenberger SJ.Donner BG. J. Org. Chem. 1993, 58: 4139 -
2i
Shie J.-J.Fang J.-M. J. Org. Chem. 2003, 68: 1158 -
2j
Medwid JB.Paul R.Baker JS.Brockman JA.Du MT.Hallett WA.Hanifin JW.Hardy RA.Tarrant ME.Torley IW.Wrenn S. J. Med. Chem. 1990, 33: 1230 -
2k
Khanna IK.Weier RM.Yu Y.Xu XD.Koszyk FJ.Collins PW.Koboldt CM.Veenhuizen AW.Perkins WE.Casler JJ.Masferrer JL.Zhang YY.Gregory SA.Seibert K.Isakson PC. J. Med. Chem. 1997, 40: 1634 -
3a
Kametani T.Takahashi K.Ohsawa T.Ihara M. Synthesis 1977, 245 -
3b
Feldhues U.Schäfer HJ. Synthesis 1982, 145 -
3c
Capdevielle P.Lavigne A.Maumy M. Synthesis 1989, 453 -
3d
Yamazaki S.Yamazaki Y. Bull. Chem. Soc. Jpn. 1990, 63: 301 -
3e
Capdevielle P.Lavigne A.Sparfel D.Baranne-Lafont J.Cuong NK.Maumy M. Tetrahedron Lett. 1990, 31: 3305 -
3f
Gao S.Herzig D.Wang B. Synthesis 2001, 544 -
3g
Chen F.-E.Kuang Y.-Y.Dai H.-F.Lu L.Huo M. Synthesis 2003, 2629 -
3h
Luca LD.Giacomelli G. Synlett 2004, 2180 -
4a
Furukawa N.Fukumura M.Akasaka T.Yoshimura T.Oae S. Tetrahedron Lett. 1980, 21: 761 -
4b
Yamazaki S.Yamazaki Y. Chem. Lett. 1990, 571 -
4c
Bose DS.Narsaiah AV. Tetrahedron Lett. 1998, 39: 6533 -
4d
Chen F.-E.Fu H.Meng G.Cheng Y.Lü Y.-X. Synthesis 2000, 1519 -
4e
Erman MB.Snow JW.Williams MJ. Tetrahedron Lett. 2000, 41: 6749 -
4f
Lai G.Bhamare NK.Anderson WK. Synlett 2001, 230 -
4g
Sharghi H.Sarvari MH. Tetrahedron 2002, 58: 10323 -
5a
Lehnert W. Tetrahedron Lett. 1971, 1501 -
5b
Campagna F.Carotti A.Casini G. Tetrahedron Lett. 1977, 1813 -
5c
Heck M.-P.Wagner A.Mioskowski C. J. Org. Chem. 1996, 61: 6486 -
5d
Nakajima N.Ubukata M. Tetrahedron Lett. 1997, 38: 2099 -
5e
Bose DS.Jayalakshmi B. J. Org. Chem. 1999, 64: 1713 -
5f
Bose DS.Narsaiah AV. Synthesis 2001, 373 -
6a
Kukhar VP.Pasternak VI. Synthesis 1974, 563 -
6b
Meshram HM. Synthesis 1992, 943 -
6c
Fukuzawa S.-I.Yamaishi Y.Furuya H.Terao K.Iwasaki F. Tetrahedron Lett. 1997, 38: 7203 -
6d
Wang E.-C.Lin G.-J. Tetrahedron Lett. 1998, 39: 4047 -
7a
Misono A.Osa T.Koda S. Bull. Chem. Soc. Jpn. 1966, 39: 854 -
7b
Misono A.Osa T.Koda S. Bull. Chem. Soc. Jpn. 1967, 40: 2875 -
7c
Talukdar S.Hsu J.-L.Chou T.-C.Fang J.-M. Tetrahedron Lett. 2001, 42: 1103 -
8a
Jereb M.Zupan M.Stavber S. Chem. Commun. 2004, 2614 -
8b
Barluenga J.Marco-Arias M.González-Bobes F.Ballesteros A.González JM. Chem. Commun. 2004, 2616 - 9
Barluenga J.González-Bobes F.Murguía MC.Ananthoju SR.González JM. Chem.-Eur. J. 2004, 10: 4206 - 10
Miller RA.Hoerrner RS. Org. Lett. 2003, 5: 285 - 11
Chen F.-E.Li Y.-Y.Xu M.Jia H.-Q. Synthesis 2002, 1804 -
12a
Togo H.Katohgi M. Synlett 2000, 565 -
12b
Togo H.Harada Y.Yokoyama M. J. Org. Chem. 2000, 65: 926 -
12c
Katohgi M.Togo H. Tetrahedron 2001, 57: 7481 -
12d
Mori N.Togo H. Synlett 2004, 880
References
CAUTION: It is known that iodine reacts with ammonia water under certain conditions to give a black powder of nitrogen triiodide monoamine (NI3·NH3). The dry powder explodes readily by mechanical shock, heat or irradiation. Although we did not have any incidents in this study, one should be careful.
14Online data from Sigma-Aldrich products;
http://www.sigmaaldrich.com/Brands/Aldrich.html