Organic iodine(I, III, and V) chemistry: 10 Years of development at the Medical University of Warsaw, Poland

Molecules

Volumn 5, Issue 12, 2000, Pages 1331-1371

  Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

(Diacetoxyiodo)arenes; (Dichloroiodo)arenes; Aromatic hypervalent iodine compounds; Aromatic oxidative iodination; Diaryliodonium salts; Iodoarenes; Iodylarenes; Oxidative anion metatheses in ionic halides

Indexed keywords

(DIACETOXYIODO)BENZENE; ACID; ANION; AROMATIC COMPOUND; BENZENE DERIVATIVE; CHROMIC OXIDE; CHROMIUM DERIVATIVE; HALIDE; HYDROGEN PEROXIDE; INORGANIC SALT; IODINE DERIVATIVE; LEAD ACETATE; MANGANESE OXIDE; MERCURY DERIVATIVE; ORGANOIODINE DERIVATIVE; OXIDIZING AGENT; PERIODATE SODIUM; PERMANGANATE POTASSIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM IODATE; UNCLASSIFIED DRUG; UREA;

ARYLATION; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMISTRY; CHLORINATION; COMPARATIVE STUDY; CONFERENCE PAPER; ENVIRONMENT; IODINATION; ISOMER; LABORATORY; LIQUID; OXIDATION; POLAND; REACTION ANALYSIS; SYNTHESIS; UNIVERSITY;

EID: 0001641195     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/51201331     Document Type: Conference Paper

References (148)

1. Krowczynski, A.; Skulski, L. p-Iodo-N-methylacetanilide and its Polyvalent Iodine Derivatives. Polish J. Chem. 1993, 67, 67-70.
2. Krassowska-Swiebocka, B.; Lulinski, P.; Skulski, L. Aromatic Iodination of Activated Arenes With Lead Tetraacetate as the Oxidant. Synthesis 1995, 926-929.
3. Kazmierczak, P.; Skulski, L. A Short-Cut Synthesis of Diaryliodonium Bromides Followed by Oxidative Anion Metatheses. Synthesis 1995, 1027-1032.
4. Farhan, A.N.; Skulski, L. 2- and 2,8-Substituted Iodine(III) Derivatives of Dibenzofuran. Polish J. Chem. 1995, 63, 1663-1668.
5. 2)-6-(aryliodonio)carbazole)Bromides. Polish J. Chem. 1996, 70, 211-216.
6. Two complementary papers: a) Farhan, A.N.; Kryska, A.; Skulski, L. Exemplary Oxidative and Evaporative Anion Metatheses in Potassium Halides. Bull. Polish Acad. Sci., Chem. 1996, 44, 201-203.
7. b) Kazmierczak, P.; Skulski, L. Oxidative Anion Metatheses in Diaryliodonium Iodides and Chlorides. Bull. Chem. Soc. Jpn. 1997, 70, 219-224.
8. Abdo Nagi Farhan (Yemen), Ph.D. thesis entitled: "Syntheses of novel aromatic iodonium salts substituted with various carbo- and heterocyclic groups" [in Polish]; Fac. of Pharm., Med. Acad., Warsaw 1996, 146 pp. + Addenda, 173 refs. Defended on March 5, 1997.
9. Lulinski, P; Skulski, L. The Direct Iodination of Arenes with Chromium(VI) Oxide as the Oxidant. Bull. Chem. Soc. Jpn. 1997, 70, 1665-1669., Erratum. See Ref. 11, p. 118.
10. Farhan, A.N.; Skulski, L.; Kryska, A. 2- and 2,7-Substituted Iodonium/Diiodonium Salts Derived from Xanthene, Xanth-9-one, Fluorene, and Fluoren-9-one. Polish J. Chem. 1997, 71, 1236-1245.
11. Kazmierczak, P.; Skulski, L. A Simple, Two-Step Conversion of Various Iodoarenes to (Diacetoxyiodo)arenes with Chromium(VI) Oxide as the Oxidant. Synthesis 1998, 1721-1723.
12. Lulinski, P; Skulski, L. Oxidative Iodination of Arenes with Manganese(IV) Oxide or Potassium Permanganate as the Oxidants. Bull. Chem. Soc. Jpn. 1999, 115-120.
13. Krassowska-Swiebocka, B.; Prokopienko, G.; Skulski, L. Biphasic Chlorination of Iodoarenes to (Dichloroiodo)arenes. Synlett 1999, 1409-1410.
14. Skulski, L.; Wroczynski, P. Improved Syntheses of Some Diaryliodonium Salts from Symmetric Diarylmercurials and (Dichloroiodo)arenes (Willgerodt Method). Bull. Polish Acad. Sci., Chem., 1999, 47, 231-238.
15. Kazmierczak, P.; Skulski, L.; Obeid, N. Oxidative Chlorination of Various Iodoarenes to (Dichloro-iodo)arenes with Chromium(VI) Oxide as the Oxidant. J. Chem. Res., Synop. 1999, 64-65.
16. Kryska, A.; Skulski, L. Improved, Acid-catalyzed Iodinating Procedures for Activated Aromatics with (Diacetoxyiodo)benzene as the Oxidant. J. Chem. Res., Synop. 1999, 590-591 and (M), 2501-2517. In its full-text version there is a review on the aromatic halogenation reactions with organic trivalent iodine reagents as the oxidants.
17. Kryska, A.; Skulski, L. Improved, Acid-catalyzed Iodinating Procedures for Activated Aromatics with (Diacetoxyiodo)benzene as the Oxidant. J. Chem. Res., Synop. 1999, 590-591 and (M), 2501-2517. In its full-text version there is a review on the aromatic halogenation reactions with organic trivalent iodine reagents as the oxidants.
18. Pawel Kazmierczak, Ph. D. thesis entitled: "New synthetic methods for preparing diaryliodonium salts, (diacetoxyiodo)arenes, and (dichloroiodo)arenes" [in Polish], Fac. of Pharm., Med. Acad., Warsaw 1999., 186 pp. + Addenda, 314 refs. Defended on December 8, 1999.
19. Lulinski, P.; Skulski, L. Iodination of Both Deactivated and Activated Arenes with Sodium Periodate or Sodium Iodate as the Oxidants. Bull. Chem. Soc. Jpn. 2000, 73, 951-956.
20. Papers in press or in preparation for publication: (a) Baranowski, A.; Plachta, D.; Skulski, L.; Klimaszewska, M. Liquid-Phase and Biphasic Chlorination of Some Iodoarenes to (Dichloroiodo)arenes with Sodium Peroxodisulfate as the Oxidant. J. Chem. Res., Synop. 2000, 435-437.
21. (b) Obeid, N.; Skulski, L. Novel Oxidatixe, Liquid-Phase Chlorination Procedures for the Preparation of (Dichloroiodo)arenes from Iodoarenes. Polish J. Chem. 2000, 74, 1609-1615.
22. (c) Lulinski, P.; Obeid, N.; Skulski, L. A One-Pot Method for Preparing (Dichloroiodo)arenes from Arenes.
23. (d) Krassowska-Swiebocka, B.; Lulinski, P.; Skulski, L. Chemical Manganese Dioxide (CMD): Its Application to Oxidative Iodination of Benzene, Halobenzenes and Some Deactivated Arenes.
24. (e) Kazmierczak, P.; Skulski, L.; Kraszkiewicz, L. A Facile Synthesis of (Diacetoxyiodo)arenes and Iodylarenes from Iodoarenes with Sodium Periodate as the Oxidant.
25. Reviews on Aromatic Iodination: (a) Roedig, A. in: Houben-Weyl, 4th ed., Vol. V/4a; ed. by E. Mueller, Stuttgart 1960, pp. 517-678.
26. (b) Merkushev, E.B. Synthesis 1988, 923.
27. (c) March, J.; Advanced Organic Chemistry, 4th ed., New York 1992., pp. 531-534.
28. (d) Grimmet, M.R. Adv. Heterocyclic Chem. 1993, 57, 291; ibid., 58, 271; ibid., 59, 245.
29. (d) Grimmet, M.R. Adv. Heterocyclic Chem. 1993, 57, 291; ibid., 58, 271; ibid., 59, 245.
30. (d) Grimmet, M.R. Adv. Heterocyclic Chem. 1993, 57, 291; ibid., 58, 271; ibid., 59, 245.
31. (e) Steel, P.G. Halobenzenes, in: Rodd's Chem. Carbon Compounds, 2nd ed., ed. by M. Sainsburry, Amsterdam 1996., Vol. 3, Part 1, pp. 178-224.
32. (f) The Merck Index, 12th ed. on CD-ROM, Merck Co. 1998.
33. (a) Nesmeyanov, A.N.; Makarova, L.G. Organic Compounds of Mercury, Amsterdam 1967.
34. (b) Makarova, L.G. in: Organometallic Reactions, ed. by E.I. Becker, M. Tsutsui, Vol. 1, New York 1970, pp. 119-348; Vol. 2, New York 1971, pp. 355-423.
35. (b) Makarova, L.G. in: Organometallic Reactions, ed. by E.I. Becker, M. Tsutsui, Vol. 1, New York 1970, pp. 119-348; Vol. 2, New York 1971, pp. 355-423.
36. (c) Mueller, E. ed., Methoden der organischen Chemie (Houben-Weyl), Vol. 13(2b), Stuttgart 1974.
37. (a) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine, Weinheim 1992.
38. (b) Varvoglis, A. Hypervalent Iodine in Organic Synthesis, San Diego 1997.
39. (c) Chemistry of Hypervalent Compounds, ed. by K. Akiba, New York 1999., Chap. 11 and 12.
40. Skulski, L.; Wroczynski, P. Polish J. Chem. 1982, 56, 975.
41. Skulski, L.; Wroczynski, P. Khim. Geterotsikl. Soed. 1983, 543.
42. Wroczynski, P.; Kujawa, A.; Skulski, L. Khim. Geterotsikl. Soed. 1985, 386.
43. Khodeir, N.M.; Skulski, L.; Wroczynski, P. Bull. Polish Acad. Sci., Chem. 1986, 34, 443.
44. Khodeir, N.M.; Skulski, L.; Wroczynski, P. Bull. Polish Acad. Sci., Chem. 1987, 35, 9.
45. Skulski, L.; Kujawa, A.; Kujawa, T.M. Bull. Polish Acad. Sci., Chem. 1987, 35, 499.
46. Skulski, L.; Kujawa, A.; Wroczynski, P. Khim. Geterotsikl. Soed. 1989, 249.
47. Kandeel, E.; Skulski, L.; Wroczynski, P. Bull. Polish Acad. Sci., Chem. 1990, 38, 37.
48. Niemyjska, M.; Skulski, L.; Zdrojewska, H. Bull. Polish Acad. Sci., Chem. 1990, 38, 41.
49. Skulski, L.; Kujawa, A.; Wroczynski, P. Bull. Polish Acad. Sci., Chem. 1991, 39, 23.
50. Baranowski, A.; Skulski, L. Bull. Polish Acad. Sci., Chem. 1991, 39, 29.
51. Skulski, L.; Baranowski, A.; Lempke, T. Bull. Polish. Acad. Sci., Chem. 1991, 39, 459.
52. Serguchev, Yu. A.; Davydowa, V.G.; Makhon'kov, D.I.; Cheprakov, A.V.; Beletskaya, I.P. Zh. Org. Khim. 1985, 21, 2010.; J. Org. Chem. USSR 1985, 21, 1841.
53. Serguchev, Yu. A.; Davydowa, V.G.; Makhon'kov, D.I.; Cheprakov, A.V.; Beletskaya, I.P. Zh. Org. Khim. 1985, 21, 2010.; J. Org. Chem. USSR 1985, 21, 1841.
54. Shimizu, A.; Yamataka, K.; Isoya, T. Bull. Chem. Soc. Jpn. 1985, 58, 1611.
55. Grigor'ev, M.G.; Buketova, I. A.; Polevshchikov, P.F. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1987, 30, 22.; Chem. Abstr. 1998, 109, 6142.
56. Grigor'ev, M.G.; Buketova, I. A.; Polevshchikov, P.F. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1987, 30, 22.; Chem. Abstr. 1998, 109, 6142.
57. Cainelli, G.; Cardillo, G. Chromium Oxidations in Organic Chemistry, Berlin 1984.
58. Chaikovskii, V.K.; Novikov, A.N. Zh. Prikl. Khim. 1984, 57, 134.; Chem. Abstr. 1984, 100, 191452.
59. Chaikovskii, V.K.; Novikov, A.N. Zh. Prikl. Khim. 1984, 57, 134.; Chem. Abstr. 1984, 100, 191452.
60. Chen, J.-A.; Lin, C.-S.; Liu, L.K. J. Chin. Chem. Soc. (Taiwan) 1996, 43, 95.
61. (a) Fieser, L.F.; Fieser, M. Reagents in Organic Synthesis, Vols. 1-18.
62. (b) Oxidation in Organic Chemistry, ed. by K.W. Wiberg, New York 1965.
63. (c) Oxidation. Techniques and Application in Organic Synthesis, ed. by R.L. Augustine, New York 1969.
64. (a) Galecki, J. Preparatyka Nieorganiczna, Warsaw 1964., p. 439.
65. (b) Karyakin, Yu.V.; Angelov, I.I. Chistye Khimicheskie Reaktivy, Moscow 1955., p. 333.
66. (a) Aoyama, T.; Sonoda, N.; Yamaguchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Schioiri, T. Synlett 1998, 35; see also Refs. 4-8 therein for their former works in which the CMD (Wako product) was used as the oxidant.
67. (b) Hirano, M.; Yakabe, S.; Hikamori, H.; Clark, J.H.; Morimoto, T. J. Chem. Res. Synop. 1998, (i) Part 1, p. 308; (ii) Part 2, p. 310; (iii) Part 3, p. 771.
68. (b) Hirano, M.; Yakabe, S.; Hikamori, H.; Clark, J.H.; Morimoto, T. J. Chem. Res. Synop. 1998, (i) Part 1, p. 308; (ii) Part 2, p. 310; (iii) Part 3, p. 771.
69. (b) Hirano, M.; Yakabe, S.; Hikamori, H.; Clark, J.H.; Morimoto, T. J. Chem. Res. Synop. 1998, (i) Part 1, p. 308; (ii) Part 2, p. 310; (iii) Part 3, p. 771.
70. (a) Fatiadi, A.J. Synthesis 1974, 229, see particularly Table 4 therein, p. 243.
71. 6 reagent.
72. Wirth, H.O.; Koenigstein, O.; Kern, W. Liebigs Ann. Chem. 1960, 634, 84.
73. (a) Keys, A.; Johnson, D. R.; Soulen, R. L. CHED Newsletter, Fall 1994, Abstr. No.72. Paper presented at a 208th National Meeting of the American Chemical Society, Washington, D.C. August 21-25, 1994.
74. (a) Keys, A.; Johnson, D. R.; Soulen, R. L. CHED Newsletter, Fall 1994, Abstr. No.72. Paper presented at a 208th National Meeting of the American Chemical Society, Washington, D.C. August 21-25, 1994.
75. (b) Brazdil, L.C.; Cutler, C.J. J. Org. Chem. 1996, 61, 9621.
76. (c) Brazdil, L.C.; Fitch, J.L.; Cutler, C.J.; Haynik, D.M.; Ace, E.R. J. Chem. Soc., Perkin Trans. 2, 1998, 933.
77. 5 reagent, see: (a) Yamada, Y.; Okawara, M. Macromol. Chem. 1972, 152, 153.
78. (b) Togo, H.; Abe, S.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1999, 72, 2351 and 2354.
79. Suzuki, H. Org. Synth. 1971, 51, 94 or Coll. Vol. VI, p.700.
80. Aldrich Catalogue Handbook of Fine Chemicals 1999-2000.
81. Chaikovskii, V.K.; Kharlova, T.S.; Filimonov, V.D.; Saryucheva, T.A. Synthesis 1999, 748.
82. Togo, H.; Nogami, G.; Yokoyama, M. Synlett 1998, 534.
83. McKillop, A.; Kemp, D. Tetrahedron 1989, 45, 3299.
84. Ogata, Y.; Aoki, K. J. Am. Chem. Soc. 1968, 90, 6187.
85. Niemyjska, M. unpublished results.
86. Keefer, R.M.; Andrews, L.J. J. Am. Chem. Soc. 1958, 80, 277.
87. Willgerodt, C. Tageblatt der 58. Vers. deutscher Naturforscher u. Aertzte, Strassburg 1885.
88. Willgerodt, C. Die organischen Verbindungen mit mehrwertigem Jod, Stuttgart 1914.
89. Lucas, H.J.; Kennedy, E.R. Org. Synth., Coll. Vol. III, New York 1955, p. 482.
90. Taylor, R.T.; Stevenson, T.A. Tetrahedron Lett. 1988, 29, 2033.
91. Zanka, A.; Takeuchi, H.; Kubota, A. Org. Process Res. Dev. 1998, 2, 270.
92. Toehl, A. Ber. dtsch. chem. Ges. 1893, 26, 2949.
93. Karele, B. Ya.; Neiland, O. Ya. Latv. PSR Zinat. Acad. Vestis, Kim. Ser. 1970, 587; Chem. Abstr. 1971, 74, 42033.
94. Karele, B. Ya.; Neiland, O. Ya. Latv. PSR Zinat. Acad. Vestis, Kim. Ser. 1970, 587; Chem. Abstr. 1971, 74, 42033.
95. Makhon'kov, D.I.; Cheprakov, A.V.; Beletskaya, I.P. Zh. Org. Khim. 1986, 22, 681.
96. Koyuncu, D.; McKillop, A.; McLaren, L. J. Chem. Res., Synop. 1990, 21.
97. Golinski, J.; Kazmierczak, P.; Skulski, L. communicated at a Meeting of the Polish Chemical Society, Krakow, September 4-7, 1991, Abstracts of Papers, (1), p. 25.
98. Nekrasov, B. Textbook of General Chemistry, Moscow 1969., p. 258.
99. Morton, J.R.; Wilcox, H.W. Inorg. Synth., Vol. 4, New York 1953., p. 48.
100. (a) Muzart, J. Synthesis 1995, 1325.
101. (b) McKillop, A.; Sanderson, W.R. Tetrahedron 1995, 51, 6145.
102. (c) McKillop, A.; Sanderson, W. R. J. Chem. Soc., Perkin Trans. 1 2000, 471.
103. Lu, C.-S.; Hughes, E.W.; Giguere, P.A. J. Am. Chem. Soc. 1941, 53, 1507.
104. (a) Stang, P.J.; Zhdankin, V.V. Chem. Rev. 1996, 96, 1123.
105. (a) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409.
106. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179.
107. (c) Muraki, T.; Togo, H.; Yokoyama, M. Rev. Heteroatom Chem. 1997, 17, 213.
108. (d) Moriarty, R.M.; Prakash, O. Adv. Heterocycl. Chem. 1998, 69, 1.
109. (e) Varvoglis, A.; Spyroudis, S. Synlett 1998, 221.
110. (f) Kirschning, A. J. Prakt. Chem./Chem.-Ztg. 1998, 340, 184.
111. (g) Ochiai, M. Kikan Kagaku Sosetsu (in Japanese) 1998, 34, 181.
112. (h) Hypervalent Organic Compounds (book in Japanese), Anon., Tokyo 1998.
113. (i) Muraki, T.; Togo, H.; Yokoyama, M. J. Org. Chem. 1999, 64, 2883.
114. (j) Wirth, T.; Hirt, V.H. Synthesis 1999, 1271.
115. (k) 2nd Symposium on Iodine Utilization, Chiba, Japan, Oct. 16, 1999, Proceedings (FIU Rep. No. 2); see pp. 5-8 and 116-136.
116. Kazmierczak, P.; Skulski, L. communicated at a Meeting of the Polish Chemical Society, Poznan, Sept. 23-26, 1996.
117. Kryska, A.; Lechnio, J.; Skulski, L. communicated at an All-Polish Meeting of Medicine Students, Warsaw, April 15-17, 1999.
118. Beringer, F.M.; Falk, R.A.; Karniol, M.; Lillien, J.; Masullo, G.; Mausner, M.; Sommer, E. J. Am. Chem. Soc. 1959, 81, 342.
119. Hartmann, C.; Meyer, V. Ber. dtsch. chem. Ges. 1894, 27, 426.
120. Sharefkin, J.G.; Saltzman, H. Org. Synth. 1963, 43, 65.
121. Banarjee, A.; Banarjee, G.C.; Bhattacharia, S.; Banarjee, S.; Sammadar, H. J. Indian Chem. Soc. 1981, 58, 605.
122. Lucas, H.J.; Kennedy, E.R. Org. Synth. 1942, 22, 72.
123. Ciustea, G. Panescu, A. Rev. Chim. (Bucharest) 1969, 20, 216.
124. Chaundhari, S.S.; Synlett 2000, 278.
125. Ireland, R.E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
126. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
127. Meyer, S.D.; Schreiber, S.L. J. Org. Chem. 1994, 59, 7549.
128. Bayraktaroglou, T.O.; Gooding, M.A.; Khatib, S.F.; Lee, M.; Kourouma, M.; Landot, R.G. J. Org. Chem. 1993, 58, 1264.
129. Olah, G.A. Halonium Ions, New York 1975.
130. Koser, G.F. Halonium Ions, in: The Chemistry of Functional Groups, Supplement D, ed. by S. Patai, Z. Rappoport, New York 1983., Chap. 25.
131. Sandin, R.B. Chem. Rev. 1943, 32, pp. 249, pp. 266.
132. Willgerodt, C. Ber. dtsch. chem. Ges. (a) 1897, 30, 56;
133. (b) 1898, 31, 915.
134. Freidlina, R. Kh.; Nesmeyanov, A.N.; Compt. Rend. [Doklady] Acad. Sci. U.R.S.S. 1940, 29, 567; Chem. Abstr. 1941, 35, 3614.
135. Freidlina, R. Kh.; Nesmeyanov, A.N.; Compt. Rend. [Doklady] Acad. Sci. U.R.S.S. 1940, 29, 567; Chem. Abstr. 1941, 35, 3614.
136. Beringer, F.M.;. Lillien, I. J. Am. Chem. Soc. 1960, 82, 725.
137. Neiland, O. Ya. Latv. PSR Zinat. Akad. Vestis, Kim. Ser. 1964, pp. 589., pp. 591.
138. Beringer, F.M.; Chang, L.L. J. Org. Chem. 1972, 37, 1516.
139. Beringer, F.M.; Briedley, A.; Drexler, M.; Gindler, E.M.; Lumpkin, C.C. J. Am. Chem. Soc. 1953, 75, 2708.
140. van der Puy, M. J. Fluorine Chem. 1982, 21, 385.
141. Kitamura, T.; Matsuyuki, J.; Taniguchi, H. Synthesis 1994, 147.
142. (a) Jurd, L. Austral. J. Sci. Res. 1949, 2[A], 595.
143. (b) Seikel, M.K. Org. Synth. 1944, 24, 47.
144. (c) Gaca, J. personal communication.
145. Forster, M.O.; Schaeppi, J.H. J. Chem. Soc. 1912, 101, 382.
146. Kryska, A.; Skulski, L. communicated at an Annual Meeting of the Polish Chemical Society, Lodz, Sept. 10-15, 2000.
147. Lucas, H. J.; Kennedy, E. R.; Formo, M. W. Org. Synth. 1942, 22, 70.
148. Kryska, A.; Lulinski, P.; Skulski, L. communicated at an Annual Meeting of the Polish Chemical Society, Lodz, Sept. 10-15, 2000.