Convenient Deuteration of Bromo Aromatic Compounds by Reductive Debromination with Sodium Amalgam in CH3OD

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1188-1190

  Miura, Yozo ^a   Oka, Hiroyuki ^a   Yamano, Eiji ^a   Morita, Masanori ^b  

^a Osaka Prefecture University   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001403874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9619037     Document Type: Article

References (24)

1. For example: Miura, Y.; Momoki, M.; Fuchikami, T.; Teki, Y.; Itoh, K; Mizutani, K. J. Org. Chem. 1996, 61, 4300.
2. Murray, A., III; Williams, D. L. Organic Syntheses with Isotopes; Interscience: New York, 1958; Part II, Chaper 16.
3. For example: (a) Weldon, L. H. P.; Wilson, C. L. J. Chem. Soc. 1946, 235. (b) Turkevich, J.; McKenzie, H. A.; Friedman, L.; Spurr, R. J. Am. Chem. Soc. 1949, 71, 4045. (c) Goubeau, J.; Luther, H.; Feldmann, K.; Brandes, G. Chem. Ber. 1953, 86, 214. (d) Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540. (e) Lauer, W. M.; Day, J. T. J. Am. Chem. Soc. 1955, 77, 1904.
4. For example: (a) Weldon, L. H. P.; Wilson, C. L. J. Chem. Soc. 1946, 235. (b) Turkevich, J.; McKenzie, H. A.; Friedman, L.; Spurr, R. J. Am. Chem. Soc. 1949, 71, 4045. (c) Goubeau, J.; Luther, H.; Feldmann, K.; Brandes, G. Chem. Ber. 1953, 86, 214. (d) Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540. (e) Lauer, W. M.; Day, J. T. J. Am. Chem. Soc. 1955, 77, 1904.
5. For example: (a) Weldon, L. H. P.; Wilson, C. L. J. Chem. Soc. 1946, 235. (b) Turkevich, J.; McKenzie, H. A.; Friedman, L.; Spurr, R. J. Am. Chem. Soc. 1949, 71, 4045. (c) Goubeau, J.; Luther, H.; Feldmann, K.; Brandes, G. Chem. Ber. 1953, 86, 214. (d) Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540. (e) Lauer, W. M.; Day, J. T. J. Am. Chem. Soc. 1955, 77, 1904.
6. For example: (a) Weldon, L. H. P.; Wilson, C. L. J. Chem. Soc. 1946, 235. (b) Turkevich, J.; McKenzie, H. A.; Friedman, L.; Spurr, R. J. Am. Chem. Soc. 1949, 71, 4045. (c) Goubeau, J.; Luther, H.; Feldmann, K.; Brandes, G. Chem. Ber. 1953, 86, 214. (d) Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540. (e) Lauer, W. M.; Day, J. T. J. Am. Chem. Soc. 1955, 77, 1904.
7. For example: (a) Weldon, L. H. P.; Wilson, C. L. J. Chem. Soc. 1946, 235. (b) Turkevich, J.; McKenzie, H. A.; Friedman, L.; Spurr, R. J. Am. Chem. Soc. 1949, 71, 4045. (c) Goubeau, J.; Luther, H.; Feldmann, K.; Brandes, G. Chem. Ber. 1953, 86, 214. (d) Hall, G. E.; Piccolini, R.; Roberts, J. D. J. Am. Chem. Soc. 1955, 77, 4540. (e) Lauer, W. M.; Day, J. T. J. Am. Chem. Soc. 1955, 77, 1904.
8. Asomaning, W. A.; Eaborn, C.; Walton, R. M. J. Chem. Soc., Perkin Trans. 2 1973, 137.
9. Müller, J. P. H.; Parlar, H.; Korte, F. Synthesis 1976, 524.
10. (a) Tashiro, M.; Iwasaki, A.; Fukata, G. J. Org. Chem. 1978, 43, 196.
11. (b) Tashiro, M.; Nakayama, K.; Fukata, G. J. Chem. Soc., Perkin Trans. 1 1983, 2315.
12. (c) Tashiro, M.; Tsuzuki, H.; Tsukinoki, T.; Mataka, S.; Nakayama, K.; Yonemitsu, T. J. Labelled Compd. Radiopharm. 1990, 28, 703.
13. (d) Tsuzuki, H.; Iyama, H.; Tsukinoki, T.; Mukumoto, M.; Yonemitsu, T.; Nagano, Y.; Thiemann, T.; Mataka, S.; Tashiro, M. J. Chem. Res. (S) 1994, (S) 302 and references cited therein.
14. Miura, Y.; Yamano, E. J. Org. Chem. 1995, 60, 1070.
15. 1H NMR spectra of the mixtures weighed.
16. We further investigated reductive dechlorination of some chloro aromatic compounds in a similar manner. While 1,4-dichlorobenzene was not subject to reductive dechlorination, 1,3-dichloro- and 1,3,5-trichlorobenzenes underwent slow reductive dechlorination to give a mixture of 1,3-dichloro- and chlorobenzenes and a mixture of 1,3,5-trichloro-, 1,3-dichloro-, and chlorobenzenes, respectively.
17. Holleman, A. F. Organic Syntheses, Wiley: New York, 1941; Collective Vol. 1, p 554. Fieser, L. F.; Fieser, M. Reagents for Organic Syntheses; Wiley: New York, 1967; Vol. 1, p 1033.
18. Holleman, A. F. Organic Syntheses, Wiley: New York, 1941; Collective Vol. 1, p 554. Fieser, L. F.; Fieser, M. Reagents for Organic Syntheses; Wiley: New York, 1967; Vol. 1, p 1033.
19. Ishida, T.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 4238. Miura, Y; Matsumoto, M.; Ushitani, Y. Macromolecules 1993, 26, 2628. Miura, Y.; Oka, H.; Momoki, M. Synthesis 1995, 1419.
20. Ishida, T.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 4238. Miura, Y; Matsumoto, M.; Ushitani, Y. Macromolecules 1993, 26, 2628. Miura, Y.; Oka, H.; Momoki, M. Synthesis 1995, 1419.
21. Ishida, T.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 4238. Miura, Y; Matsumoto, M.; Ushitani, Y. Macromolecules 1993, 26, 2628. Miura, Y.; Oka, H.; Momoki, M. Synthesis 1995, 1419.
22. Hurtley, W. H. J. Chem. Soc. 1901, 79, 1293.
23. Elmorsy, S. S.; Pelter, A.; Smith, K. Tetrahedron Lett. 1991, 32, 4175.
24. Dimroth, K.; Berndt, A.; Reichardt, C. Organic Syntheses; Wiley: New York, 1969; Vol. 49, p 114.