Partial oxidation of alkenylsilanes with ozone: A novel stereoselective approach to the diol and triol derivatives

Synthesis

Volumn , Issue 10, 2008, Pages 1641-1645

  Igawa, Kazunobu ^a   Sakita, Kyohei ^b   Murakami, Masanori ^b   Tomooka, Katsuhiko ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenes; Oxidations; Ozonolysis; Peroxides; Silicon

Indexed keywords

ADDITION REACTIONS; AIR POLLUTION; GASES; OZONE; PEROXIDES;

C C BONDS; FORMYL GROUP; GOOD YIELDS; NUCLEOPHILIC ADDITIONS; PARTIAL OXIDATION (POX); STEREO-SELECTIVE;

OXIDATION;

CARBON; FUNCTIONAL GROUP; OZONE; PEROXIDE; SILANE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY;

EID: 44949233104     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032161     Document Type: Article

References (13)

1. For leading reviews on ozonolysis and other ozone oxidations, see: (a) Bailey, P. S. Ozonation in Organic Chemistry, Olefinic Compounds, Vol. 1; Academic Press: London, 1978.
2. (b) Bailey, P. S. Ozonation in Organic Chemistry, Nonolefinic Compounds, Vol. 2; Academic Press: London, 1982.
3. Theoretical studies suggest that the formation of primary ozonide is a rate-determining step for the ozonolysis of alkenes. For a representative example, see: Anglada, M. J.; Crehuet, R.; Bofill, J. M. Chem. Eur. J. 1999, 5, 1809.
4. Murakami, M.; Sakita, K.; Igawa, K.; Tomooka, K. Org. Lett. 2006, 8, 4023.
5. Büchi and Wüest reported the ozonization of trimethylsilyl-substituted alkenes in the 1970s, in which they proposed a similar silyl peroxide as an intermediate, see: Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1978, 100, 294.
6. 2 or hexane in 10-30% yields.
7. (a) Castrantas, H. M.; Banerjee, D. K.; Noller, D. C. Fire and Explosion Hazards of Peroxy Compounds, ASTM STP 394; American Society for Testing and Materials: Philadelphia PA, 1965.
8. (b) Castrantas, H. M.; Banerjee, D. K. Laboratory Handling and Storage of Peroxy Compounds, ASTM STP 471; American Society for Testing and Materials: Philadelphia PA, 1970.
9. 4 but also to purification on silica gel, most probably due to the bulky silyl group on the peroxide moiety. Furthermore, slow thermal degradation was observed at >80°C in thermogravimetric analysis (TGA) of 2c and 4q; see ref. 3.
10. (a) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
11. (b) Igawa, K.; Tomooka, K. Angew. Chem. Int. Ed. 2006, 45, 232.
12. A related reduction of silyl peroxide in a norcamphor derivative has been reported, see: Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437.
13. Cyclic peroxide has been utilized as a synthetic equivalent of ketone, see: Singh, C.; Malik, H. Org. Lett. 2005, 7, 5673.