Ring-opening reactions of alkanone acetals with iodosilane equivalents for the formation of siloxyalkyl enol ethers

Chemistry Letters

Volumn , Issue 7, 2001, Pages 740-741

  Ohshita, Joji ^a   Iwata, Arihiro ^a   Tang, Heqing ^a   Yamamoto, Yasushi ^b   Matui, Chinami ^b   Kunai, Atsutaka ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b SHIN ETSU CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035640214     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.740     Document Type: Article

References (13)

1. G. L. Larson, "The Chemistry of Organic Silicon Compounds," ed. by S. Patai and Z. Rappoport, Wiley, New York (1989), Part 1, Chap. 11.
2. E. W. Colvin, "Silicon Reagents in Organic Synthesis", Academic Press, London (1988).
3. J. Ohshita, A. Iwata, F. Kanetani, A. Kunai, Y. Yamamoto, and C. Matui, J. Org. Chem., 64, 8024 (1999).
4. Y. Yamamoto, H. Shimizu, C. Matui, and M. Chinda, Main Group Chemistry , 1, 409 (1996).
5. Y. Yamamoto, H. Shimizu, and Y. Hamada, J. Organomet. Chem., 509, 119 (1996).
6. Y. Yamamoto and C. Matui, Organometallics, 16, 2204 (1997).
7. A. Kunai, T. Sakurai, E. Toyoda, and M. Ishikawa, Organometallics, 13, 3233 (1994).
8. It has been reported that mixtures of chlorosilanes and NaI in acetonitrile work as synthetic equivalents of iodosilanes. See, a) T. Morita, Y. Okamoto, and H. Sakurai, J. Syn. Org. Chem., 39, 973 (1981).
9. b) H. Sakurai and Y. Okamoto, J. Syn. Org. Chem., 40, 525 (1982).
10. 2Si: C, 61.63; H, 10.34%. Found: C, 61.51; H, 10.49%.
11. M. E. Jung, W. A. Andrus, P. L. Ornstein, Tetrahedron Lett., 1977, 4175.
12. R. D. Miller and D. R. McKean, Tetrahedron Lett., 1982, 323.
13. The reaction of alkanone acetals with reagent 1b proceeded in a different fashion from those with 1a, producing iodides arising from coupling of two units of the acetals. For example, compound 4 was obtained from the reaction of cyclohexanone ethylene acetal with 1b in 63% isolated yield. The details will be reported elsewhere. (equation presented)