Synthesis of hydroximoyl chlorides from aldoximes and benzyltrimethylammonium tetrachloroiodate (BTMA ICl4)

Tetrahedron

Volumn 56, Issue 8, 2000, Pages 1057-1064

  Kanemasa, Shuji ^a   Matsuda, Haruhiko ^b   Kamimura, Akio ^c   Kakinami, Takaaki ^d  

^a KYUSHU UNIVERSITY   (Japan)

^b Grad Sch Eng Sci   (Japan)

^c YAMAGUCHI UNIVERSITY   (Japan)

^d UBE NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Aldoximes; Benzyltrimethylammonium tetrachloroiodate; Hydroximoyl chlorides

Indexed keywords

CHLORINE DERIVATIVE; IODATE; OXIME DERIVATIVE; TRIMETHYLAMMONIUM SALT DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; CONTROLLED STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034681343     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01047-9     Document Type: Article

References (25)

1. (a) Quilico, A. In Five and Six Membered Compounds with Nitrogen and Oxygen; Wiley, R. H., Ed.; Interscience Publishers: New York, 1962.
2. (b) Caramella, P.; Grünanger P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392.
3. (c) Torssell, K. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
4. (d) Grünanger, P.; Vita-Finzi, P. Isoxazoles-Part 1; Chemistry of Heterocyclic Compounds, Vol. 49; Wiley: New York, 1991 and references cited therein.
5. (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598.
6. (b) Bianchi, G.; Gandolfi, R.; Grünanger P. The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; Suppl. C, Part 2, pp 752-773.
7. (c) Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410-416.
8. (d) Kanemasa, S.; Tsuge, O. Heterocycles 1990, 30, 719-736.
9. (e) Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G. W. Adv. Heterocycl. Chem. 1994, 60, 261-327.
10. Kanemasa S., Nishiuchi M., Kamimura A., Hori K. J. Am. Chem. Soc. 116:1994;2324-2339.
11. (a) Kajigaeshi, S.; Kakinami, T. J. Syn. Org. Chem. Jpn. 1993, 51, 366-376.
12. (b) Kajigaeshi, S.; Kakinami, T. Benzyltrimethylammonium tetrachloroiodate. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Sussex, 1995; pp 384-385.
13. (c) Kajigaeshi, S.; Kakinami, T.; Okamoto, T.; Fujisaki, S. Halogenation and Oxidation with Quaternary Ammonium Polyhalides; 1996, Chapter 4, pp 125-176.
14. E-1a: mp 108-110°C; Z-1a: mp 79-80°C. Pure E-1a is obtained after crystallization, but it gradually isomerizes at room temperature to Z-1a resulting in an E/Z-mixture.
15. Although not isolated, the crude reaction mixture from 1g includes lachrymatory compound(s).
16. Kajigaeshi S., Shinmasu Y., Fujisaki S., Kakinami T. Chem. Express. 5:1990;141-144.
17. Kajigaeshi S., Moriwaki M., Fujisaki S., Kakinami T. Chem. Express. 6:1991;185-188.
18. Okamoto T., Kakinami T., Fujimoto H., Kajigaeshi S. Bull. Chem. Soc. Jpn. 64:1991;2566-2568.
19. 4.
20. Liu K.-C., Shelton B.R., Howe R.K. J. Org. Chem. 45:1980;3916-3918.
21. (a) Walter, W.; Schaumann, E. Synthesis 1971, 111-130.
22. (b) Armand, par J. Bull. Soc. Chim. Fr. 1966, 882-888.
23. Kanemasa S., Norisue Y., Suga H., Tsuge O. Bull. Chem. Soc. Jpn. 61:1988;3973-3982.
24. Numata T., Itoh O., Yoshimura T., Oae S. Bull. Chem. Soc. Jpn. 56:1983;257-265.
25. 4.