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 2002(8): 1065-1071
DOI: 10.1055/s-2002-31950
DOI: 10.1055/s-2002-31950
PAPER
© Georg Thieme Verlag Stuttgart · New York
Convenient One-pot Procedure for Converting Aryl Sulfides to Nitroaryl Sulfones
Further Information
Received
12 February 2002
Publication Date:
03 June 2002 (online)
Publication History
Publication Date:
03 June 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200208/lookinside/thumbnails/10.1055-s-2002-31950-1.jpg)
Abstract
When treated with nitrogen dioxide and ozone in inert solvent at 0 °C or below, aryl sulfides underwent smooth oxidative nitration to give nitroaryl sulfones in good yield. Using this methodology, a series of mono- and di-nitrated aryl sulfones were prepared from methyl phenyl sulfide and diphenyl sulfide and their physical data are presented.
Key words
nitro compounds - sulfones - sulfides - nitration - nitrogen oxides - ozone
-
1a
Uehata K.Kawakami T.Suzuki H. J. Chem. Soc., Perkin Trans. 1 2002, 696 -
1b
Kawakami T.Suzuki H. J. Chem. Soc., Perkin Trans. 1 2000, 1259 -
1c
Kawakami T.Suzuki H. J. Chem. Soc., Perkin Trans. 1 2000, 3640 -
1d
Suzuki H.Kawakami T. J. Org. Chem. 1999, 64: 3361 -
1e
Kawakami T.Suzuki H. Tetrahedron Lett. 1999, 40: 1157 -
2a
Courtin A. Helv. Chim. Acta 1981, 64: 1849 -
2b
Olah GA.Orlinkov A.Oxyzoglou AB.Prakash GKS. J. Org. Chem. 1995, 60: 7348 -
2c
Koloneitsev A.Movchun VN.Kondratenko NV.Yagupolski YL. Synthesis 1990, 1151 -
3a
Ono M.Nakamura Y.Sato S.Itoh I. Chem. Lett. 1988, 395 -
3b
Takubo Y. J. Pharm. Soc. Jpn. 1942, 62: 518 -
4a
Baker BR.Kadish AF.Querry MV. J. Org. Chem. 1950, 15: 400 -
4b
Loudon JD. J. Chem. Soc. 1936, 218 -
5a
Michel K.Matter M. Helv. Chim. Acta. 1961, 44: 2204 -
5b
Johnson FE.Hamilton CS. J. Am. Chem. Soc. 1949, 71: 74 - 6 For a review of preparative methods, see
Schank K. In Houben-Weyl’s Methoden der Organischen Chemie Vol. E11/2.:Klamann D. Georg Thieme; Stuttgart: 1985. p.1132-1298 - 7
Ciocca B.Canonica L. Gazz. Chim. Ital. 1946, 76: 113 - For a survey of the Kyodai-nitration, see
-
8a
Nonoyama N.Mori T.Suzuki H. Zh. Org. Khim. 1998, 34 1591, -
8b
Ridd JH. Acta Chem. Scand. 1998, 52: 11 -
8c
Suzuki T.Noyori R. Chemtracts 1997, 10: 813 -
8d
Mori T.Suzuki H. Synlett 1995, 383 -
8e
Matsunaga M. Chimica Oggi 1994, 58 - 9 For oxidation of sulfides with nitrogen dioxide, see
Buddenberg O. In Houben-Weyl’s Methoden der Organischen Chemie Vol. 4/1a:Muller E.Bayer O. Georg Thieme; Stuttgart: 1981. p.809-811 - 10
Horner L.Schaefer H.Ludwig H. Chem. Ber. 1958, 91: 75 -
11a
Suzuki H.Murashima T. J. Chem. Soc., Perkin Trans. 1 1994, 903 -
11b
Suzuki H.Murashima T.Tatsumi A.Kozai I. Chem. Lett. 1993, 1421 - 12
Yagupolsky LM.Marenets MS. J. Gen. Chem. U.S.S.R. 1956, 26: 99 - 13
Kornblum N.Cheng L.Kerber RC.Kestner MM.Newton BN.Pinnick HW.Smith RG.Wade PA. J. Org. Chem. 1976, 41: 1560 - 14
Rabai J.Kapovits I.Tanacs B.Tamas J. Synthesis 1990, 847 - 15
Buehler CA.Masters JE. J. Org. Chem. 1938, 4: 262 - 16
Andersen KK.Edmonds WH.Biasotti JB.Strecker RA. J. Org. Chem. 1966, 31: 2859 - 17
Foster GF.Reid EE. J. Am. Chem. Soc. 1924, 46: 1936 - 18
Waldron WR.Reid EE. J. Am. Chem. Soc. 1923, 45: 2404 - 19
Adams R.Reifschneider W.Nair MD. Croat. Chem. Acta 1957, 29: 277 , Chem. Abstr. 1959, 53, 16146a - 20
Su W. Tetrahedron Lett. 1994, 28: 4955 - 21
Tanikaga R.Kaji A. Bull. Chem. Soc. Jpn. 1973, 46: 3814 - 22
Kolomeitsev AA.Movchun VN.Kondratenko NV.Yagupolski YuL. Synthesis 1990, 1151