2-chloro-1,3-dimethylimidazolinium chloride. 3. Utility for chlorination, oxidation, reduction, and rearrangement reactions

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5832-5835

  Isobe, Toshio ^a   Ishikawa, Tsutomu ^b  

^a Shiratori Pharmaceutical Co Ltd   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 1,3 DIMETHYLIMIDAZOLINIUM CHLORIDE; ALCOHOL; AMIDE; CARBAMIC ACID DERIVATIVE; HYDROXAMIC ACID; KETONE; OXIME; REAGENT; SULFIDE; UNCLASSIFIED DRUG; UREA;

ARTICLE; CHEMICAL REACTION; CHLORINATION; DEHYDRATION; OXIDATION; REACTION ANALYSIS; REDUCTION;

EID: 0033529733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990211q     Document Type: Article

References (32)

1. Isobe, T.; Ishikawa, T. see the preceding papers; (a) Part 1. (b) Part 2.
2. Bolmann, R. In Comprephensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 204-206.
3. Reference to the product in run 3 in Table 1 is as follows: d'Engenieres, M. D.; Miocque, M.; Gautier, J.-A. Bull. Soc. Chim. Fr. 1964, 2471.
4. References to the products in Table 2 are as follows: (a) run 1; Gruber, L.; Tomoskozi, I.; Radics, L. Synthesis 1975, 708. (b) run 2; Bateman, L.; Shipley, F. W. J. Chem. Soc. 1955, 1996. (c) run 3; Isobe, T.; Soeda, Y.; Saito, M.; Suzuki, S. Jpn. Kokai Tokkyo Koho JP 04 308547, 1992; Chem. Abstr. 1993, 118, 233484.
5. References to the products in Table 2 are as follows: (a) run 1; Gruber, L.; Tomoskozi, I.; Radics, L. Synthesis 1975, 708. (b) run 2; Bateman, L.; Shipley, F. W. J. Chem. Soc. 1955, 1996. (c) run 3; Isobe, T.; Soeda, Y.; Saito, M.; Suzuki, S. Jpn. Kokai Tokkyo Koho JP 04 308547, 1992; Chem. Abstr. 1993, 118, 233484.
6. References to the products in Table 2 are as follows: (a) run 1; Gruber, L.; Tomoskozi, I.; Radics, L. Synthesis 1975, 708. (b) run 2; Bateman, L.; Shipley, F. W. J. Chem. Soc. 1955, 1996. (c) run 3; Isobe, T.; Soeda, Y.; Saito, M.; Suzuki, S. Jpn. Kokai Tokkyo Koho JP 04 308547, 1992; Chem. Abstr. 1993, 118, 233484.
7. March, J. In Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; pp 1081-1083.
8. References to the products in Table 3 are as follows: (a) run 4; Yamamoto, Y. Yakugaku Zasshi 1953, 73, 938; Chem. Abstr. 1954, 48, 10739. (b) run 5; Sasson, Y.; Rempel, G. L. Can. J. Chem. 1974, 52, 3825.
9. References to the products in Table 3 are as follows: (a) run 4; Yamamoto, Y. Yakugaku Zasshi 1953, 73, 938; Chem. Abstr. 1954, 48, 10739. (b) run 5; Sasson, Y.; Rempel, G. L. Can. J. Chem. 1974, 52, 3825.
10. References to the products in Table 3 are as follows: (a) run 4; Yamamoto, Y. Yakugaku Zasshi 1953, 73, 938; Chem. Abstr. 1954, 48, 10739. (b) run 5; Sasson, Y.; Rempel, G. L. Can. J. Chem. 1974, 52, 3825.
11. Tidwell, T. T. Org. React. 1990, 39, 297.
12. Angyal, S. J. Org. React. 1954, 8, 197.
13. References to the products in Table 5 are as follows: (a) runs 2 and 3; Ho, T.-L.; Hall, T.-W.; Wong, C. M. Synthesis 1973, 206. (b) run 4; Vowinkel, E. Synthesis 1974, 430.
14. References to the products in Table 5 are as follows: (a) runs 2 and 3; Ho, T.-L.; Hall, T.-W.; Wong, C. M. Synthesis 1973, 206. (b) run 4; Vowinkel, E. Synthesis 1974, 430.
15. Wallis, E. S.; Lane, J. F. Org. React. 1946, 3, 267. Smith, P. A. S. Org. React. 1946, 3, 337.
16. Wallis, E. S.; Lane, J. F. Org. React. 1946, 3, 267. Smith, P. A. S. Org. React. 1946, 3, 337.
17. References to the products in Table 6 are as follows: (a) run 1; Davis, T. L.; Constan, N. D. J. Am. Chem. Soc. 1936, 58, 1800. (b) run 2; Carothers, W. H.; Jones, G. A. J. Am. Chem. Soc. 1925, 47, 3051. (c) run 3; Davis, T. L.; Blanchard, K. C. Org. Synth. Coll. Vol. I 1941, 453. (d) run 4; Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 07 89926, 1995; Chem. Abstr. 1995, 123, 111681. (e) run 5; Skita, A.; Rolfes, H. Chem. Ber. 1920, 53, 1242.
18. References to the products in Table 6 are as follows: (a) run 1; Davis, T. L.; Constan, N. D. J. Am. Chem. Soc. 1936, 58, 1800. (b) run 2; Carothers, W. H.; Jones, G. A. J. Am. Chem. Soc. 1925, 47, 3051. (c) run 3; Davis, T. L.; Blanchard, K. C. Org. Synth. Coll. Vol. I 1941, 453. (d) run 4; Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 07 89926, 1995; Chem. Abstr. 1995, 123, 111681. (e) run 5; Skita, A.; Rolfes, H. Chem. Ber. 1920, 53, 1242.
19. References to the products in Table 6 are as follows: (a) run 1; Davis, T. L.; Constan, N. D. J. Am. Chem. Soc. 1936, 58, 1800. (b) run 2; Carothers, W. H.; Jones, G. A. J. Am. Chem. Soc. 1925, 47, 3051. (c) run 3; Davis, T. L.; Blanchard, K. C. Org. Synth. Coll. Vol. I 1941, 453. (d) run 4; Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 07 89926, 1995; Chem. Abstr. 1995, 123, 111681. (e) run 5; Skita, A.; Rolfes, H. Chem. Ber. 1920, 53, 1242.
20. References to the products in Table 6 are as follows: (a) run 1; Davis, T. L.; Constan, N. D. J. Am. Chem. Soc. 1936, 58, 1800. (b) run 2; Carothers, W. H.; Jones, G. A. J. Am. Chem. Soc. 1925, 47, 3051. (c) run 3; Davis, T. L.; Blanchard, K. C. Org. Synth. Coll. Vol. I 1941, 453. (d) run 4; Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 07 89926, 1995; Chem. Abstr. 1995, 123, 111681. (e) run 5; Skita, A.; Rolfes, H. Chem. Ber. 1920, 53, 1242.
21. References to the products in Table 6 are as follows: (a) run 1; Davis, T. L.; Constan, N. D. J. Am. Chem. Soc. 1936, 58, 1800. (b) run 2; Carothers, W. H.; Jones, G. A. J. Am. Chem. Soc. 1925, 47, 3051. (c) run 3; Davis, T. L.; Blanchard, K. C. Org. Synth. Coll. Vol. I 1941, 453. (d) run 4; Isobe, T.; Hosogai, A. Jpn. Kokai Tokkyo Koho JP 07 89926, 1995; Chem. Abstr. 1995, 123, 111681. (e) run 5; Skita, A.; Rolfes, H. Chem. Ber. 1920, 53, 1242.
22. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
23. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
24. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
25. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
26. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
27. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
28. References to the products in Table 7 are as follows: (a) run 1; Hofmann, A. W. Ann. 1850, 74, 1. (b) run 2; Meiser, W. Chem. Ber. 1899, 32, 2049. (c) run 3; Oeda, H. Bull. Chem. Soc. Jpn. 1935, 10, 531. (d) run 4; Van Zyl, G.; Langenberg, R. J.; Tan, H. H.; Schut, R. N. J. Am. Chem. Soc. 1956, 78, 1955. (e) run 5; Huang, X.; Keillor, J. W. Tetrahedron Lett. 1997, 38, 313 (f) run 6; Kienzle, F. Tetrahedron Lett. 1972, 1771. (g) run 7; Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827.
29. Heldt, W. Z. Org. React. 1960, 11, 1. Gawley, R. E. Org. React. 1988, 35, 1.
30. Heldt, W. Z. Org. React. 1960, 11, 1. Gawley, R. E. Org. React. 1988, 35, 1.
31. Reference to the product in run 4 in Table 8 is as folows: Dickerman, S. C.; Besozzi, A. J. J. Org. Chem. 1954, 19, 1855.
32. Kusama, H.; Uchiyama, K.; Yamashita, Y.; Narasaka, K. Chem. Lett. 1995, 715.