Transformation of 1-alkyl-substituted indene ozonides and the corresponding solvent-derived ozonolysis products to tricyclic peroxides: Isolation and characterization of novel hexoxecane derivatives

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2093-2096

  Ushigoe, Yoshihiro ^a   Kawamura, Shin Ichi ^a   Teshima, Koichi ^a   Nojima, Masatomo ^a   McCullough, Kevin J ^b  

^a OSAKA UNIVERSITY   (Japan)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE;

ARTICLE; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0029987744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00201-8     Document Type: Article

References (15)

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2. (a) Patai, S. ed., 'The Chemistry of Peroxides,' Wiley, New York, 1983.
3. (b) Ando, W. ed., 'Organic Peroxides', Wiley, New York, 1992.
4. (a.) McCullough, K. J.;. Teshima, K; M. Nojima, J. Chem. Soc., Chem. Commun., 1993, 931.
5. (b) Ushigoe, Y. ; Tanaka, S.;. Nojima, M; McCullough, K. J. Tetrahedron Lett., 1994, 52, 9741 and references therein.
6. Teshima, K.; Kawamura, S.; Ushigoe, Y.; Nojima, M.; McCullough, K. J. J. Org. Chem., 1995, 60, 4755.
7. For the synthesis of other hexoxecane derivatives, see (a) Rio, G.; Rio, M. J. J. Chem. Soc., Chem. Commun., 1982, 72.
8. (b) Golnick, K.; Griesbeck, A. Angew. Chem., 1983, 95, 751.
9. (c) Griesbaum, K.; Kiesel, G.; Mertens, H.; Krieger-Beck, P.; Henke, H. Can. J. Chem., 1994, 72, 2198.
10. 2) 486.
11. The yields of dimers 4b-d from their respective precursors are shown in brackets: (i) 4b (41%) from 5b; (ii) 4c (14%) from 3c and (40%) from 5c; (iii) 4d (14%) from 3d and (31%) from 5d. For 3c and 3d, the unreacted ozonide was recovered in ca. 40% in each case.
12. w were 0.048 and 0.120 respectively for 2771 intensities with I > 2σ(I)
13. Stewart, J. J. P. J. Comput. Chem., 1989, 10, 209, 221.
14. Still, W. C., Columbia University, 1990.
15. Sheldrick, G. M., University of Göttingen, 1994.