Oxidative Anion Metatheses in Diaryliodonium Iodides and Chlorides

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 1, 1997, Pages 219-224

  Kaźmierczak, Pawel ^a   Skulski, Lech ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041110632     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.219     Document Type: Article

References (31)

1. G. A. Olah, "Halonium Ions," Wiley, New York (1975).
2. a) G. F. Koser, "Halonium Ions," in "The Chemistry of Functional Groups, Supplement D," ed by S. Patai and Z. Rappoport, Wiley, New York (1983), Chap, 25;
3. b) G. F. Koser, in "The Chemistry of Halides, Pseudo-Halides and Azides, Supplement D2," ed by S. Patai and Z. Rappoport, Wiley-Interscience, Chichester (1995), Chap. 21.
4. a) A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine," VCH, New York (1992);
5. b) P. J. Stang and V. V. Zhdankin, "Organic Polyvalent Iodine Compounds," Chem. Rev., 96, 1123 (1996).
6. T. M. Kasumov, V. K. Brel, A. S. Koz'min, and N. S. Zefirov, Synthesis, 1995, 775.
7. A. Varvoglis, Synthesis, 1984, 709, pp. 713-717.
8. F. M. Beringer, M. Drexler, E. M. Gindler, and Ch. C. Lumpkin, J. Am. Chem. Soc., 75, 270 (1953).
9. T. Kitamura, J. Matsuyuki, and H. Taniguchi, Synthesis, 1994, 147.
10. P. Kaźmierczak and L. Skulski, Synthesis, 1995, 1027.
11. a) M. K. Seikel, Org. Synth., Wiley, New York (1994), Vol. 24, p. 47;
12. b) L. Jurd. Aust. J. Sci. Res., 2[A], 595 (1949);
13. c) B. V. Suvorov and N. R. Bukeikhanov, "Okislitel'nye Reaktsii v Organicheskom Sinteze," Khimiya, Moscow (1978), pp. 173-183;
14. d) N. I. Rudakova, O. V. Anufrieva, and E. A. Smirnova, Zh. Obshch. Khim., 62, 290 (1992), (see also Refs. 2, 3, 4, 5, 6, and 7 therein), Chem. Abstr., 122, 31241 (1995);
15. d) N. I. Rudakova, O. V. Anufrieva, and E. A. Smirnova, Zh. Obshch. Khim., 62, 290 (1992), (see also Refs. 2, 3, 4, 5, 6, and 7 therein), Chem. Abstr., 122, 31241 (1995);
16. e) H. Scheider, Ger. Patent DE 4442808 (1995); Chem. Abstr., 124, 29603 (1996);
17. e) H. Scheider, Ger. Patent DE 4442808 (1995); Chem. Abstr., 124, 29603 (1996);
18. f) J. Gaca, personal communication.
19. It is also possible to steam-distill off the diiodine evolved, with leaving the metathesized iodonium salts in the remainders. This workup is, however, less effective and time-consuming.
20. 2. Similar pathways (a) and (b) are very likely encountered in the oxidative metatheses of diaryliodonium bromides and chlorides into the other salts.
21. It is known that both diaryliodonium and tetraalkylammonium iodides are easily converted into the respective dihaloiodates(I) either by the reaction of dichlorine or dibromine with iodides, or by the reaction of IBr or ICI with the corresponding bromides or chlorides. For more details see Ref. 3, Chap. 7.
22. A. N. Farhan, A. Kryska, and L. Skulski. "Communication at a Meeting of the Polish Chemical Society," September25-28. Lublin (1995).
23. F. M. Geringer, E. J. Gering, I. Kuntz, and M. Mausner, J. Am. Chem. Soc., 60, 141 (1956).
24. C. M. Wheeler, Jr., and R. A. Sandstedt, J. Am. Chem. Soc., 77, 2024 (1955).
25. M. O. Forster and J. H. Schaeppi, J. Chem. Soc., 101, 382 (1912).
26. F. D. Chattaway and G. Hoyle, J. Chem. Soc., 123, 654 (1923).
27. F. M. Beringer and E. M. Gindler, Iodine Abstr. Rev., 3, 70 (1956).
28. J. L. Dektar and N. P. Hacker, J. Org. Chem., 55, 639 (1990).
29. N. S. Zefirov, T. M. Kasumov, A. S. Koz'min, V. D. Sorokin, P. J. Stang, and V. V. Zhdankin, Synthesis, 1993, 1209.
30. N. S. Zefirov, G. A. Sereda, S. E. Sosonuk, N. V. Zyk, and T. I. Likhomanova, Synthesis, 1995, 1359.
31. "Dictionary of Organic Compounds," 6th ed. Chapman and Hall, London-Glasgow-Weinheim-New York-Tokyo-Melbourne-Madras (1996).