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Metody syntezy sulfidów fenylowo-fluorometylowych

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Warianty tytułu
EN
The metods of synthesis of phenyl-fluoromethyl sulfides
Języki publikacji
PL
Abstrakty
EN
Aromatic compounds containing halogenomethylsulfonyl or halogenomethylsulfanyl group are often biologically active as fungicides or herbicides [1–6]. Especially important plant protection agents are fluorine compounds [7–12]. Through to specific activity in living organisms, fluorine compounds found wide application. One of the reasons of high activity of these compounds is their high lipophilicity, which provides increase of solubility in lipides. Due to this fact absorption of fluorine compounds is easier and their transport in organism is faster what increase their efficiency [13–15]. In this paper the methods of synthesis of aromatic compounds containing fluoromethylsulfanyl group are described. Aryl-fluoromethyl sulfides can be easily transformed into sulfones by oxidation [16–18]. Methods of preparation of aryl-fluoromethyl sulfides can be divided into three groups: 1. Fluorination of methylsulfanyl group [19–31] 2. Substitution of chlorine atom into fluorine in phenyl-chloromethyl sulfides [32–34] 3. Fluoromethylation of phenylothiols [35, 36].
Rocznik
Strony
983--994
Opis fizyczny
Bibliogr. 37 poz., schem.
Twórcy
autor
autor
  • Wydział Chemiczny, Politechnika Warszawska ul. Noakowskiego 3, 00-664 Warszawa
Bibliografia
  • [1] Patent USA US 2.484.489, 1949.
  • [2] Patent niemiecki, DE 100.768, 1957.
  • [3] Patent brytyjski, GB 875.533, 1960.
  • [4] Patent japoński, JP 7.990.145, 1979.
  • [5] Patent polski, PL 202 745 B1, 2009.
  • [6] M. Krawczyk, Z. Zimińska, Z. Ochal, A.Mizerski, D. Kalhorn, Pol. J. Appl. Chem., 2003, 47, 155.
  • [7] B. Malichenko, L.M. Yagupolskii, Ukr. Khim. Zh., 1968, 34, 486.
  • [8] Patent japoński, JP 7.594.126, 1975.
  • [9] Patent japoński, JP 61.221.170, 1986.
  • [10] Patent niemiecki, DE 3.621.301, 1988.
  • [11] Patent polski PL 195 100 B1, 2007.
  • [12] The Pesticide Manual, A World Compendium,13 th. edition, The British Crop Protection Council, Farnham, UK, 2003.
  • [13] M. Schlosser, Tetrahedron, 1978, 34, 3.
  • [14] R.E. Banks, Organofluorine Chemicals and Their Industrial Applications, Ellis Horowood Ltd., Chichester 1979.
  • [15] R. Filler, Y.Kobayashi, Biochemical Aspects of Fluorine Chemistry, Kadania Ltd., Elsevier Biochemical Press, Tokyo 1982.
  • [16] B.M. Trost, D.P. Curran, Tetrahedron Lett., 22, 1287 (1981).
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  • [18] J. Eisch, M. Behrooz, S.K. Dua, J. Organomet. Chem., 1985, 285, 121.
  • [19] M. Zupan, J. Fluor. Chem., 1976, 8, 305.
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  • [22] J.R. McCarthy, N.P. Peet, M.E. LeTourneau, M. Inbasekaran, J. Am. Chem. Soc., 1985, 107, 735.
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  • [24] Patent japoński, JP 62.181.230, 1988.
  • [25] T. Umemoto, G. Tomizawa, J. Org. Chem., 1995, 60, 3563.
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  • [28] S. Furuta, M. Kuroboshi, T. Hiyama, Tetrahedron Lett., 1995, 36, 8243.
  • [29] S. Furuta, M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn., 1998, 71, 2687.
  • [30] N. Yoneda, T. Fukuhara, Chem. Lett., 2001, 3, 222.
  • [31] S. Ayuba, N. Yoneda, T. Fukuhara, S. Hara, Bull. Chem. Soc. Jpn., 2002,75, 1603.
  • [32] Patent USA, US 7.265.247, 2007.
  • [33] K.M. Moore, J. Wemple, Synthesis, 1977, 11, 791.
  • [34] D.P. Matthews, J.R. McCarthy, Org. Prep. Proced. Int. 1994, 26, 605.
  • [35] Patent USA, 9,323,370, 1993.
  • [36] W. Zhang, L. Zhu, J. Hu, Tetrahedron, 2007, 63, 10569.
  • [37] G.K. Surya Prakash, I. Ledneczki, S. Chacko, G.A. Olah, Org. Lett., 2008, 10, 557.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS8-0005-0027
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