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-00000084.xml
Synthesis 2003(7): 1055-1064
DOI: 10.1055/s-2003-39163
DOI: 10.1055/s-2003-39163
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Esters and Amides from Activated Alcohols using Manganese(IV) Dioxide: Tandem Oxidation Processes
Further Information
Received
25 February 2003
Publication Date:
09 May 2003 (online)
Publication History
Publication Date:
09 May 2003 (online)
Abstract
Manganese(IV) dioxide can be used in conjunction with sodium cyanide in THF-methanol or in methanol alone for the direct conversion of activated alcohols into methyl esters. Ethyl and isopropyl esters can also be prepared. Similarly, use of manganese(IV) dioxide and sodium cyanide in THF containing ammonia or primary amines can be used to convert alcohols into the corresponding amides. Several activated alcohols and one non-activated alcohol example are reported.
Key words
alcohols - amides - esters - oxidations - tandem reactions
- For activated alcohols see:
-
1a
Wei X.Taylor RJK. Tetrahedron Lett. 1998, 39: 3815 -
1b
Blackburn L.Wei X.Taylor RJK. Chem. Commun. 1999, 1337 -
1c
Wei X.Taylor RJK. J. Org. Chem. 2000, 65: 616 -
1d
Runcie KA.Taylor RJK. Chem. Commun. 2002, 9: 974 -
1e
Blackburn L.Kanno H.Taylor RJK. Tetrahedron Lett. 2003, 44: 115 -
1f For non-activated alcohols,
see:
Blackburn L.Pei C.Taylor RJK. Synlett 2002, 215 -
2a
Blackburn L.Taylor RJK. Org. Lett. 2001, 3: 1637 -
2b
Kanno H.Taylor RJK. Tetrahedron Lett. 2002, 43: 7337 - 3
Kanno H.Taylor RJK. Synlett 2002, 1287 - 4
McAllister GD.Wilfred CD.Taylor RJK. Synlett 2002, 1291 - 5
Corey EJ.Gilman NW.Ganem BE. J. Am. Chem. Soc. 1968, 90: 5616 - 6
Gilman NW. J. Chem. Soc., Chem. Commun. 1971, 733 - 7
Foot JS.Kanno H.Giblin GMP.Taylor RJK. Synlett 2002, 1293 -
8a For
a mechanistic explanation, see:
Breslow R.Schmuck C. Tetrahedron Lett. 1996, 37: 8241 -
8b For recent use in synthesis,
see:
Ragharan S.Anuradha K. Tetrahedron Lett. 2002, 43: 5181 - 9
Papaioannou D.Francis GW.Aksnes DW.Maartmann-Moe K.Brekke T. Acta Chem. Scand. 1990, 44: 90 - 10
Holland HL.Kindermann M.Kumaresan S.Stefanac T. Tetrahedron: Asymmetry 1993, 4: 1353 - 11
Noureldin NA.Zhao D.Lee DG. J. Org. Chem. 1997, 62: 8767 - 12
Hans JJ.Driver RW.Burke SD. J. Org. Chem. 2000, 65: 2114 - 13
Bauer R.Remiger P.Wagner H. Phytochemistry 1989, 28: 505 - 14
Dietz B.Bauer R. Pharm. Biol. 2001, 39: 11 - 15
Stöhr JR.Xiao PG.Bauer R. Planta Med. 1999, 65: 175 - 17
Keck GE.McLaws MD.Wager TT. Tetrahedron 2000, 56: 9875 - 18
Patil VJ.Maevers U. Tetrahedron Lett. 1996, 37: 1281 - 19
Nilsson K.Ullenius C.Krause N. J. Am. Chem. Soc. 1996, 118: 4194 - 20
Avila-Zarraga JG.Martinez R. Synth. Commun. 2001, 31: 2177 - 21
Kuhn G. J. Am. Chem. Soc. 1948, 70: 3370 - 22
Lai G.Anderson WK. Synth. Commun. 1997, 27: 1281 - 23
Thiele R. Justus Liebigs Ann. Chem. 1899, 306: 215 - 24
Rhee H.Kim JY. Tetrahedron Lett. 1998, 39: 1365 - 25
Hecht K. Tetrahedron Lett. 1973, 1397 - 26
Batori S.Doepp D.Messmer A. Tetrahedron 1994, 50: 4699 - 27
Krapcho AP.Waterhouse DJ.Hammach A.Domenico R.Menta E. Synth. Commun. 1997, 27: 781 - 28
Anderson B. J. Am. Chem. Soc. 1958, 80: 992 - 29
Moulines F.Ruiz J.Astruc D. J. Organomet. Chem. 1988, 340: C13 - 30
Qian C.Wang L. Tetrahedron 2000, 51: 7193 - 31
Shono T.Ishige O.Uyama H.Kashimura S. J. Org. Chem. 1986, 51: 546 - 32
Gajida T.Zwierzak B. Synthesis 1981, 1005 - 33
Anker L.Lauterwein J.van de Waterbeemd H.Testa B. Helv. Chim. Acta 1984, 67: 706 - 34
Abramovitch RA.Alvernhe G.Bartnik R.Dassanayake NL.Inbasekaran MN.Kato S. J. Am. Chem. Soc. 1981, 103: 4558 - 35
Whitehouse DL.Nelson KH.Savinov SN.Löwe RS.Austin DJ. Bioorg. Med. Chem. 1998, 6: 1273 - 36
Huisgen R.Remlinger H. Justus Liebigs Ann. Chem. 1956, 599: 177 - 37
Auzeil N.Largeron M.Fleury M. J. Chem. Soc., Perkin Trans. 2 1999, 1703 - 38
Carloni P.Eberson L.Greci L.Sgarabotto P.Stipa P. J. Chem. Soc., Perkin Trans. 2 1996, 1297 - 39
Padwa A.Austin DJ.Price AT.Weingarten MD. Tetrahedron 1996, 52: 3247 - 40
Suezawa H.Tsuchiya K.Tahara E.Hirota M. Bull. Chem. Soc. Jpn. 1987, 60: 3973 - 41
Alonso E.Ramon DJ.Yus M. Tetrahedron 1998, 54: 13629 - 42
Lluch A.-M.Gibert M.Sanchez-Baeza F.Messeguer A. Tetrahedron 1996, 52: 3973 - 43
Agwanda VC. J. Chem. Eng. Data 1984, 29: 235 - 44
Herbst RM.Roberts CW.Givens HTF.Harvill EK. J. Org. Chem. 1952, 17: 262 - 45
Huang Z.Wen L.Huang X. Synth. Comm. 1990, 20: 2579 - 46
Hoberg H.Riegel HJ. J. Organomet. Chem. 1983, 241: 245 - 47
Degani I.Dughera S.Fochi R.Serra E. Synthesis 1999, 1200 - 48
Abarbri M.Parrain JL.Duchêne A. Synth. Commun. 1998, 28: 239
References
2,4-Dodecadien-1-ol purchased from Fluka, cat. no. 00554.