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 2001(11): 1645-1648
DOI: 10.1055/s-2001-16760
DOI: 10.1055/s-2001-16760
PAPER
© Georg Thieme Verlag Stuttgart · New York
Heterogeneous Permanganate Oxidation of Styrene and Cinnamic Acid Derivatives: A Simple and Effective Method for the Preparation of Benzaldehydes
Further Information
Received
8 January 2001
Publication Date:
28 September 2004 (online)
Publication History
Publication Date:
28 September 2004 (online)
![](https://www.thieme-connect.de/media/synthesis/200111/lookinside/thumbnails/10.1055-s-2001-16760-1.jpg)
Abstract
Styrene and cinnamic acid derivatives yield correspondingly substituted benzaldehydes when oxidized by permanganate under heterogeneous conditions. Reaction of terminal aliphatic alkenes under similar conditions gives discouragingly low yields; however, ketones and ketols are obtained in very good yields from the oxidation of 2,2-disubstituted and trisubstituted alkenes, respectively. Alumina and Amberlite IR-120 can be used as solid supports in these reactions with equally good results.
Key words
oxidation - styrene - cinnamic acid - benzaldehyde - permanganate - heterogeneous - solid support
- 1
Lee DG.Chen T. In Comprehensive Organic Synthesis Vol. 7:Trost BM. Pergamon; Oxford: 1991. p.541-591 - 2
Berglund RA. In Encyclopedia of Reagents for Organic Synthesis Vol. 6:Paquette LA. Wiley; New York: 1995. p.3837-3843 - 3
Martin VS.Palazon JM.Rodriguez CM. In Encyclopedia of Reagents for Organic Synthesis Vol. 6:Paguette LA. Wiley; New York: 1995. p.4415-4422 - 4
March J. Advanced Organic Chemistry Wiley; New York: 1992. p.1181 - 5
Arndt D. Manganese Compounds as Oxidizing Agents in Organic Chemistry Open Court; LaSalle IL: 1981. p.241-246 - 6
Noureldin NA.Lee DG. J. Org. Chem. 1982, 47: 2790 -
7a
Noureldin NA.Zhao D.Lee DG. J. Org. Chem. 1997, 62: 8767 -
7b
Zhao D.Lee DG. Synthesis 1994, 915 - 8
Noureldin NA.McConnell WB.Lee DG. Can. J. Chem. 1984, 62: 2113 - 9
Noureldin NA.Caldwell M.Hendry J.Lee DG. Synthesis 1998, 1587 -
10a
Harris CE.Chrisman W.Bickford SA.Lee LY.Torreblanca AE.Singaram B. Tetrahedron Lett. 1997, 38: 981 -
10b
Sreekumar R.Padmakumar R. Tetrahedron Lett. 1997, 38: 5143 -
11a
Joshi PL.Hazra BG. J. Chem. Res. (S) 2000, 38 -
11b
Parish EJ.Li S. J. Chem. Res. (S) 1996, 288 -
11c
Salvador JAR.Sa e Melo ML.Campos Neves AS. Tetrahedron Lett. 1996, 37: 687 -
11d
Das J.Chandrasekaran S. Tetrahedron 1994, 50: 11709 -
11e
Lee DG.Chen T.Wang Z. J. Org. Chem. 1993, 58: 2918 -
11f
Baskaran S.Islam I.Vankar PS.Chandrasekaran S. J. Chem. Soc., Chem. Commun. 1992, 626 -
11g
Baskaran S.Islam I.Vankar PS.Chandrasekaran S. J. Chem. Soc., Chem. Commun. 1990, 1670 -
11h
Syamala MS.Das J.Baskaran S.Chandrasekaran S. J. Org. Chem. 1992, 57: 1928 -
11i
Baskaran S.Das J.Chandrasekaran S. J. Org. Chem. 1989, 54: 5182 - 12
Lee DG.Noureldin NA. J. Am. Chem. Soc. 1983, 105: 3188 -
13a
Prabhakaran PW.Venkatachalam S.Ninan KN. European Polymer J. 1999, 35: 1743 -
13b
Abraham S.Rajan PK.Sreekumar K. Polymer J. 1997, 29: 12