Direct formation of organomanganese bromides using Rieke manganese

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2197-2200

  Kim, Seung Hoi ^a   Hanson, Mark V ^a   Rieke, Reuben D ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANOMANGANESE COMPOUND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029880915     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00258-4     Document Type: Article

References (18)

1. For a review, see Rieke, R. D. Crit. Rev. Surf. Chem. 1991, 1, 131-166. and references cited therein.
2. (a) Rieke, R. D.; Hudnall, P.M. J.Am.Chem.Soc. 1972, 94, 7178.
3. (b) Rieke, R. D.; Uhm, S.J.; Hudnall, P. M. J. Chem. Soc. Chem. Commun. 1973, 269.
4. (c) Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
5. (d) Rieke, R. D.; Li, P. J.; Burns, T. P.; Uhm, S. J. J. Org. Chem. 1981, 46, 4342.
6. (a) Rieke, R.D. Top. Curr. Chem.59, 1, 1975.
7. (b) Rieke, R. D.Acc. Chem. Res.10, 301, 1977, and references therein.
8. (c) Arnold, R. T.; Kulenovic, S. T. Synth. Commun. 1977, 223.
9. (a) Oilman, H.; Bailie, J. C. J. Org. Chem. 1937, 2, 84.
10. (b) Gilman, H.; Kirby, R. J. Am. Chem Soc. 1941, 63, 2046.
11. (a) For a review, see Normant, J. F.; Cahiez, G. Modern Synthetic Methods; John Wiley & Sons Inc., Chichester, 1983, vol 3; pp.172-216 and references cited therein.
12. (b) Cahiez, G.; Chavant, P. Y.; Metais, E. Tetrahedron Lett. 1992, 33, 5245.
13. (c) Cahiez, G.; Laboqe, B. Tetrahedron Lett. 1989, 30, 7369.
14. In typical preparation, lithium (9.68 mmol), naphthalene (1.48 mmol), anhydrous manganese chloride (4.71 mmol) under argon were stirred in freshly distilled THF (10 mL) for 3 h at room temperature.
15. Cahiez, G.; Chavant, P. Y. Tetrahedron Lett. 1989, 30, 7373.
16. After the oxidative addition of 0.8 equiv. of organohalide to 1.0 equiv. of active manganese was totally completed, 0.3 equiv. of 1,2-dibormoethane was added to consume the remaining manganese metal. We did not observed the formation of homocoupling product of benzoyl chloride under these reaction conditions.
17. (a) Gronowitz, S. and Hakansson, R. Arkiv. Kemi. 1959, 17, 73 - 82.
18. (b) Gronowitz, S. OrganicSulphur Chemistry - Structure, Mechanism, and Synthesis; Stering, C.J.M., Butterworths. 1975; pp.203 - 228.