FORMATION OF DIARYLIODONIUM SALTS AND IODYLOARENES AND THEIR USE IN MODERN ORGANIC SYNTHESIS
DOI:
https://doi.org/10.56782/pps.44Keywords:
diaryliodonium salts, iodylarenesAbstract
Organic hypervalent iodine compounds are known for more than a century, but their importance in modern organic synthesis has been noticeably grown during last 20 years. Recently a lot of results on different properties of each class of these compounds were reported (types of bonds, spectroscopy, photochemistry and electrochemistry).
From the pharmaceutical point of view antimicrobial properties seem to be promising. Organic compounds of pentavalent iodine are used in pharmaceutical synthesis as mild and selective oxidants of alcohols. The idea of environment-friendly deactivation of ecologically dangerous phosphoorganic compounds (e.g. sarin, soman, tabun, VX) by iodyloderivates can also be connected with general healthcare problems.
Topics presented in the paper are: synthesis of diaryliodonium salts and iodyloarenes, their use in modern organic synthesis and nomenclature of organic iodine derivates.
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References
L. Skulski, Organic Iodine (I, III and V) Chemistry: 10 Years ofDevelopment at the Medical University of Warsaw, Poland,Molecules 2000, 5, 1331. Internet: http://www.mdpi.org/molecules/papers/51201331.pdf DOI: https://doi.org/10.3390/51201331
C. Willgerodt, J. Prakt. Chem. 1886, 33, 154. DOI: https://doi.org/10.1002/prac.18860330117
C. Willgerodt, Die organischen Verbindungen mit mehrwertigemJod, Enke Verlag, Stuttgart, 1914.
A. Varvoglis, The Organic Chemistry of Policoordinated Iodine,VCH, NY, 1992.
P.J. Stang, V.V. Zhdankin, Chem. Rev. 1996, 96, 1123. DOI: https://doi.org/10.1021/cr940424+
PTChem, Nomenklatura związków organicznych, PWN, Warszawa,1992.
H.J. Lucas, E.R. Kennedy, Org. Synth. 1942, 22, 72. DOI: https://doi.org/10.15227/orgsyn.022.0072
D.H.R. Barton, W.B. Motherwell, S.Z. Zard, Tetrahedron Lett.1983, 24, 5227. DOI: https://doi.org/10.1016/S0040-4039(00)88403-8
A. Banerjee, G.C. Banerjee, S. Bhattacharya, S. Banerjee, H.Sammadar, J. Indian Chem. Soc. 1981, 58, 605-607.
R.L. Datta, J.K. Chourny, J. Am. Chem. Soc. 1916, 38, 1079. DOI: https://doi.org/10.1021/ja02262a015
T.O. Bayraktaroglou, M.A. Gooding, S.F. Khatib, M. Lee, M.Kourouma, R.G. Landot, J. Org. Chem. 1993, 58, 1264. DOI: https://doi.org/10.1021/jo00057a047
J. Goliński, P. Kaźmierczak, L. Skulski, komunikat na ZjeździePTChem, Kraków, 4-7.IX.1991.
G. Ortoleva, Gazz. Chim. Ital. 1900, 30, 1.
Z. Gakovic, K.J. Morgan, J. Chem. Soc. B. 1967, 416. DOI: https://doi.org/10.1039/j29670000416
A.R. Katritzky, G.P. Savage, J.K. Gallos, H.D. Durst, Org. Prep.Proced. Int. 1989, 21, 157. DOI: https://doi.org/10.1080/00304948909356361
J.G. Sharefkin, H. Saltzman, Org. Synth. 1963, 43, 65. DOI: https://doi.org/10.15227/orgsyn.043.0065
J. Baeseken, Ch. Schneider, Proc. Acad. Science 1932, Amsterdam,
, 1140; Chem Abstr. 1933, 27, 1331. DOI: https://doi.org/10.3412/jsb1928.27.11_1331
R.J. Kennedy, A.M. Stock, J. Org. Chem. 1960, 25, 1901. DOI: https://doi.org/10.1021/jo01081a019
M. Frigerio, M. Sanragostino, S. Sputore, J. Org. Chem. 1999, 64,4537. DOI: https://doi.org/10.1021/jo9824596
Ł. Kraszkiewicz, praca magisterska: Nowa metoda otrzymywaniajodyloarenów przy użyciu nadjodanu sodowego jako utleniacza,Wydz. Farm., A.M. Warszawa 1999/2000.
P. Kaźmierczak, L. Skulski, Ł. Kraszkiewicz, Molecules 2001, 6, 881.Internet: http://www.mdpi.org/molecules/papers/61100881.pdf DOI: https://doi.org/10.3390/61100881
Ł. Kraszkiewicz, L. Skulski, ARKIVOC 2003 (vi), 120. Internet:http://www.arkat-usa.org/ark/journal/2003/Varvoglis/AV657A/AV-657A.htm DOI: https://doi.org/10.3998/ark.5550190.0004.614
A. Varvoglis, Hypervalent iodine in organic synthesis, AcademicPress, San Diego, 1997.
a) P. Kaźmierczak, L. Skulski, Synthesis 1995, 1027. b) P.Kaźmierczak, L. Skulski, Bull. Chem. Soc. Jpn. 1997, 70, 219. DOI: https://doi.org/10.1055/s-1995-4045
V.V. Zhdankin, P.J. Stang, Recent Developments in the Chemistryof Polyvalent Iodine Compounds, Chem. Rev. 2002, 102, 2523. DOI: https://doi.org/10.1021/cr010003+
M.J. Peacocok, D. Pletcher, Tetrahedron Lett. 2000, 41, 8995. DOI: https://doi.org/10.1016/S0040-4039(00)01620-8
T. Kitamura, M. Kotani, Y. Fujiwara, Tetrahedron Lett. 1996, 37,3721. DOI: https://doi.org/10.1016/0040-4039(96)00668-5
M. Ochiai, M. Toyonari, T. Sueda, Y. Kitagawa, Tetrahedron Lett.1996, 37, 8421. DOI: https://doi.org/10.1016/0040-4039(96)01926-0
M.F. Beringer, R.A. Falk, M. Karniol, I. Lillien, G. Masullo, M.Mausner, E. Sommer, J. Am. Chem. Soc. 1959, 81, 342. DOI: https://doi.org/10.1021/ja01511a020
I. Masson, E. Race, J. Chem. Soc. 1937, 1718. DOI: https://doi.org/10.1039/jr9370001718
M.F. Beringer, M. Drexler, E.M. Gindler, C.C. Lumpkin, J. Am.Chem. Soc. 1953, 75, 2705. DOI: https://doi.org/10.1021/ja01107a046
A. Dibbo, L. Stephenson, T. Walker, W.K. Warburton, J. Chem. Soc.B. 1961, 2645. DOI: https://doi.org/10.1039/jr9610002645
S. Gronowitz, B. Holm, Synth. Commun. 1974, 4, 63. DOI: https://doi.org/10.1002/chin.197306244
F.M. Beringer, R.A. Nathan, J. Org. Chem. 1970, 35, 2095. DOI: https://doi.org/10.1021/jo00831a113
F.M. Beringer, R.A. Nathan, J. Org. Chem. 1969, 34, 685. DOI: https://doi.org/10.1021/jo01255a044
H.J. Frohn, wyniki niepublikowane (na podstawie [4]).
J. Cornforth, D.D. Ridley, A.F. Sierakowski, D. Uguen, T.W.Wallace, P.B. Hitchcock, J. Chem. Soc., Perkin Trans. 1 1982,2317. DOI: https://doi.org/10.1039/p19820002317
C. Hartmann, V. Meyer, Ber. Dtsch. Chem. Ges. 1894, 27, 426. DOI: https://doi.org/10.1002/cber.18940270183
R.A. Wiley, M.A. Salter, J. Med. Chem. 1966, 9, 228. DOI: https://doi.org/10.1021/jm00320a017
C. Willgerodt, Ber. Dtsch. Chem. Ges. (a) 1897, 30, 56; (b) 1898,31, 915. DOI: https://doi.org/10.1002/cber.189803101170
L. Skulski, P. Wroczyński, Bull. Polish Acad. Sci., Chem. 1999, 47,231.
A. Shah, V.W. Pike, D.A. Widdowson, J. Chem. Soc, Perkin Trans. 11997, 2463.
M.A. Carroll, V.W. Pike, D.A. Widdowson, Tetrahedron Lett. 2000,41, 5393. DOI: https://doi.org/10.1016/S0040-4039(00)00861-3
A. Kryska, L. Skulski, Molecules 2001, 6, 875. Internet:http://www.mdpi.org/molecules/papers/61100875.pdf DOI: https://doi.org/10.3390/61100875
D.B. Dess, J.C. Martin, J. Org. Chem. 1983, 48, 4155. DOI: https://doi.org/10.1021/jo00170a070
S.D. Meyer, S.I. Schreiber, J. Org. Chem. 1993, 59, 7549. DOI: https://doi.org/10.1021/jo00103a067
H. Morales-Rijas, R.A. Moss, Chem. Rev. 2002, 102, 2497. DOI: https://doi.org/10.1021/cr9405462
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