The selective monohalogenation of dihydro- and trihydrosilanes

Microchemical Journal

Volumn 55, Issue 2, 1997, Pages 222-234

  Gansle, Paul B ^a   Gruber, Brian C ^a   Jarvis, James T ^a   Slaitas, Andis ^a   De Jesus, Senamarie ^a   De Jesus, Karl ^a  

^a IDAHO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007306406     PISSN: 0026265X     EISSN: None     Source Type: Journal    
DOI: 10.1006/mchj.1996.1417     Document Type: Article

References (25)

1. Bonini, B. F., Maiero, S., Mazzanti, G., Zani, P., Tetrahedron Lett. 32, 6801 (1991); Stang, P. J., and Learned, A. E., J. Org. Chem. 54, 1779 (1989); Jung, M. E., and Hogan, K. T., Tetrahedron Lett. 29, 6199 (1988); Larson, G. L., and Torres, E., J. Organomet. Chem. 293, 19 (1985); Maryanoff, C. A., and Maryanoff, B. E. in "Asymmetric Synthesis," (J. D. Morrison, J. W. Scott, Eds.), Vol. 4, p. 355. Academic Press, San Diego, 1984 and references therein.
2. Bonini, B. F., Maiero, S., Mazzanti, G., Zani, P., Tetrahedron Lett. 32, 6801 (1991); Stang, P. J., and Learned, A. E., J. Org. Chem. 54, 1779 (1989); Jung, M. E., and Hogan, K. T., Tetrahedron Lett. 29, 6199 (1988); Larson, G. L., and Torres, E., J. Organomet. Chem. 293, 19 (1985); Maryanoff, C. A., and Maryanoff, B. E. in "Asymmetric Synthesis," (J. D. Morrison, J. W. Scott, Eds.), Vol. 4, p. 355. Academic Press, San Diego, 1984 and references therein.
3. Bonini, B. F., Maiero, S., Mazzanti, G., Zani, P., Tetrahedron Lett. 32, 6801 (1991); Stang, P. J., and Learned, A. E., J. Org. Chem. 54, 1779 (1989); Jung, M. E., and Hogan, K. T., Tetrahedron Lett. 29, 6199 (1988); Larson, G. L., and Torres, E., J. Organomet. Chem. 293, 19 (1985); Maryanoff, C. A., and Maryanoff, B. E. in "Asymmetric Synthesis," (J. D. Morrison, J. W. Scott, Eds.), Vol. 4, p. 355. Academic Press, San Diego, 1984 and references therein.
4. Bonini, B. F., Maiero, S., Mazzanti, G., Zani, P., Tetrahedron Lett. 32, 6801 (1991); Stang, P. J., and Learned, A. E., J. Org. Chem. 54, 1779 (1989); Jung, M. E., and Hogan, K. T., Tetrahedron Lett. 29, 6199 (1988); Larson, G. L., and Torres, E., J. Organomet. Chem. 293, 19 (1985); Maryanoff, C. A., and Maryanoff, B. E. in "Asymmetric Synthesis," (J. D. Morrison, J. W. Scott, Eds.), Vol. 4, p. 355. Academic Press, San Diego, 1984 and references therein.
5. Bonini, B. F., Maiero, S., Mazzanti, G., Zani, P., Tetrahedron Lett. 32, 6801 (1991); Stang, P. J., and Learned, A. E., J. Org. Chem. 54, 1779 (1989); Jung, M. E., and Hogan, K. T., Tetrahedron Lett. 29, 6199 (1988); Larson, G. L., and Torres, E., J. Organomet. Chem. 293, 19 (1985); Maryanoff, C. A., and Maryanoff, B. E. in "Asymmetric Synthesis," (J. D. Morrison, J. W. Scott, Eds.), Vol. 4, p. 355. Academic Press, San Diego, 1984 and references therein.
6. Gevorgyan, V., Borisova, L., Popelis, J., Lukevics, E., Foltynowics, Z., Gulinski, J., and Marciniec, B., J. Organomet. Chem. 424, 15 (1992); Kobayashi, K., Kato, T., Masuda, S., Chem. Lett. 101, (1987); Kobayashi, K., Kato, T., and Masuda, S., "Kenkyu Shuroku-Ashikaga Kogyo Daigaku" Vol. 107 (CA Vol. 108, 219449e); Bertrand, G., Dubac, J., Mazerolles, P., and Ancelle, J., J. Nouv. J. Chim. 6, 381 (1982).
7. Gevorgyan, V., Borisova, L., Popelis, J., Lukevics, E., Foltynowics, Z., Gulinski, J., and Marciniec, B., J. Organomet. Chem. 424, 15 (1992); Kobayashi, K., Kato, T., Masuda, S., Chem. Lett. 101, (1987); Kobayashi, K., Kato, T., and Masuda, S., "Kenkyu Shuroku-Ashikaga Kogyo Daigaku" Vol. 107 (CA Vol. 108, 219449e); Bertrand, G., Dubac, J., Mazerolles, P., and Ancelle, J., J. Nouv. J. Chim. 6, 381 (1982).
8. Gevorgyan, V., Borisova, L., Popelis, J., Lukevics, E., Foltynowics, Z., Gulinski, J., and Marciniec, B., J. Organomet. Chem. 424, 15 (1992); Kobayashi, K., Kato, T., Masuda, S., Chem. Lett. 101, (1987); Kobayashi, K., Kato, T., and Masuda, S., "Kenkyu Shuroku-Ashikaga Kogyo Daigaku" Vol. 107 (CA Vol. 108, 219449e); Bertrand, G., Dubac, J., Mazerolles, P., and Ancelle, J., J. Nouv. J. Chim. 6, 381 (1982).
9. Gevorgyan, V., Borisova, L., Popelis, J., Lukevics, E., Foltynowics, Z., Gulinski, J., and Marciniec, B., J. Organomet. Chem. 424, 15 (1992); Kobayashi, K., Kato, T., Masuda, S., Chem. Lett. 101, (1987); Kobayashi, K., Kato, T., and Masuda, S., "Kenkyu Shuroku-Ashikaga Kogyo Daigaku" Vol. 107 (CA Vol. 108, 219449e); Bertrand, G., Dubac, J., Mazerolles, P., and Ancelle, J., J. Nouv. J. Chim. 6, 381 (1982).
10. Reddy, S. C., and De Jesus, K., J. Organomet. Chem., in press.
11. Corriu, R. J. P., and Moreau, J. J. E., J. Organomet. Chem. 20, 337 (1976); Corriu, R. J. P., and Moreau, J. J. E., Tetrahedron Lett. 4469 (1973).
12. Corriu, R. J. P., and Moreau, J. J. E., J. Organomet. Chem. 20, 337 (1976); Corriu, R. J. P., and Moreau, J. J. E., Tetrahedron Lett. 4469 (1973).
13. Dolgov, B. N., Kharitonov, N. P., and Voronkov, M. G., Zhur. Obshei Khim. 24, 861 (1954) (CA 57, 8094).
14. Jenkins, J. W., and Post, H. W., J. Org. Chem. 15, 556 (1950).
15. Miller, W. S., Peake, J. S., and Nebergall, W. H., J. Amer. Chem., Soc. 79, 5604 (1957).
16. Horner, L., and Balzer, W. D., Tetrahedron Lett. 1157 (1965); Fritzsche, H., Hasserodt, V., and Korte, F., Chem. Ber. 97, 1988 (1964).
17. Horner, L., and Balzer, W. D., Tetrahedron Lett. 1157 (1965); Fritzsche, H., Hasserodt, V., and Korte, F., Chem. Ber. 97, 1988 (1964).
18. Sommer, L. H., "Stereochemistry, Mechanism and Silicon," p. 110. McGraw-Hill, New York, 1965.
19. Chan, T. H., Melnyk, A., and Harpp, D. N., Tetrahedron Lett. 201 (1969).
20. Adam, W., Mello, R., and Curci, R., Angew. Chem. Int. Ed. Engl. 29, 890 (1990).
21. Doyle, M. P., and West, C. T., J. Amer. Chem. Soc. 97, 3777 (1975).
22. 2 to polyhydrosilanes. It is unlikely that this reagent can be modified into an optically active one and for that reason it was not studied. See Kunai, A., Kawakami, T., Toyoda, E., and Ishikawa, M., Organometallics 11, 2708 (1992).
23. Polinski, T., J. Chem. Soc., Perkin Trans. I 629 (1988). Ziegler, K., Spath, A., Schaaf, E., Schumann, W., and Winkelmann, E., Ann. Chem. 551, 109 (1942).
24. Polinski, T., J. Chem. Soc., Perkin Trans. I 629 (1988). Ziegler, K., Spath, A., Schaaf, E., Schumann, W., and Winkelmann, E., Ann. Chem. 551, 109 (1942).
25. Nagai, Y., Matsumoto, H., Hayashi, M., Tajima, E., and Watanabe, H., Bull. Chem. Soc. Jpn. 44, 3113 (1971).