Synthesis of hydrolytically stable TBDMS derivatives of hydroxynaphthoquinones

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1850-1853

  Bakola Christianopoulou, Maria N ^a   Apazidou, Katerina K ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043175030     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9511455     Document Type: Article

References (25)

1. Stone, F. G. A., West, R., Eds.; Advances in Organometallic Chemistry, Academic Press: New York, 1980; Vol. 18, p 275.
2. (a) Andersen, N. E.; Weinshenker, N. M. U.S. Patent 3,764,673; 1973. Chem. Abstr. 1974, 80, 6947.
3. (b) Crowe, A. J. Chem. Ind. (London) 1983, 304.
4. (a) Arcamone, F.; Cassinelli, G.; Fautini, G.; Grein, A.; Orezzi, P.; Pol, C.; Spalla, C. Biotechnol. Bioeng. 1969, 11, 1101.
5. (b) Lin, A. J.; Sartorelli A. C. J. Org. Chem. 1973, 38, 813.
6. (c) Khadem, El. H. S., Ed. Anthracvcline Antibiotics; Academic Press, New York, 1982.
7. d) Williamson, D. E.; Eyerett, G. W., Jr. J. Am. Chem. Soc. 1975, 97, 2397.
8. (a) Bakola-Christianopoulou, M. N. J. Organomet. Chem. 1986, 308, C24.
9. (b) J. Mol. Catal. 1991, 65, 307.
10. (a) Bakola-Christianopoulou, M. N.; Papageorgiou, V. P.; Apazidou, K. K. J. Chromatogr. 1993, 645, 293.
11. (b) Bakola-Christianopoulou, M. N ; Papageorgiou, V. P.; Apazidou, K. K. Phosphorus, Sulfur Silicon 1994, 88, 53.
12. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
13. Mawhinney, T. P.; Madson, M. A. J. Org. Chem. 1982, 47, 3336.
14. Donike, M.; Zimmermann, J. J. Chromatogr. 1980, 202, 483.
15. Olah, G. A.; Surya Prakash, G. K. S.; Krisnamurti, R. Adv. Silicon. Chem. 1991, 1, 1.
16. Formation of the TBDMS derivatives of a number of inorganic acids and of their ammonium salts by their reaction with MTBSTFA has been reported in: Mawhinney, T. P. J. Chromatogr. 1983, 257, 37.
17. All physical and spectral data obtained for MTFA and TBDMSI were consistent with the literature ones (a) Bissell, E. R.; Finger, M. J. Org. Chem. 1959, 24, 1256. (b) Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M.; Yamamoto, Y. Organometallics 1994, 13, 3233.
18. All physical and spectral data obtained for MTFA and TBDMSI were consistent with the literature ones (a) Bissell, E. R.; Finger, M. J. Org. Chem. 1959, 24, 1256. (b) Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M.; Yamamoto, Y. Organometallics 1994, 13, 3233.
19. Detty, M. R. J. Org. Chem. 1980, 45, 924.
20. Jung, M. E.; Ornstein, P. L. Tetrahedron Lett. 1977, 2659.
21. Detty, M. R.; Seidler, M. D. J. Org. Chem. 1981, 46, 1283.
22. Kirk-Othmer, Encyclopedia of Chemical Technology, 2nd ed.: John Wiley & Sons Inc.: New York, 1963; Vol. 2, p 320.
23. Olah, G. A.; Arvanaghi, M.; Vankar, Y. D. J. Org. Chem. 1980, 45, 3531.
24. (a) Tocik, Z.; Earl, R. A.; Beranek, J. Nucl. Acids Res. 1980, 8, 475.
25. (b) Tocik, Z.; Beranek, J. Nucl. Acids Res. 1981, 9, 37.