High pressure synthesis of new silicon containing heteroatom analogues of fused norbornenes

Synlett

Volumn , Issue 3, 1999, Pages 351-353

  Kirin, Srećko I ^a   Klärner, Frank Gerrit ^b   Eckert Maksíc, Mirjana ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

7 silanorbornenes; 7 oxanorbornenes; Diels Alder reaction; High pressure chemistry; Siloles

Indexed keywords

SILICON;

ARTICLE; CHEMICAL REACTION; HYPERBARISM; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0344061516     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2596     Document Type: Article

References (17)

1. (a) Ciobanu, M.; Matsumoto, K.; Liebigs Ann./Recueil 1997, 623-635.
2. (b) Isaacs, N. S.; In High Pressure Techniques in Chemistry and Physics. A Practical Approach; Holzapfel, W. B.; Isaacs, N. S., (Eds.); Oxford University Press, Oxford, 1997; pp. 307-329.
3. (c) Klärner, F.-G.; Diedrich, M. K.; In The Chemistry of the Functional Groups: The Chemistry of Dienes and Polyenes; Rappoport, Z., (Ed.); Wiley-Interscience, New York, 1997; pp. 547-617.
4. See for example: (a) Klärner, F.-G.; Diedrich, M.K.; Wigger, A. E.; In Chemistry Under Non-Classic Conditions; van Eldik, R; Hubbard, C. D., (Eds.); Spektrum Akademischer Verlag, Heidelberg and John Wiley & Sons, New York, 1997; pp. 103-161.
5. (b) Matsumoto, K.; Toda, M.; Uchida, T.; In Organic Synthesis at High Pressure; Matsumoto, K.; Morrin Acheson, R., (Eds.); John Wiley & Sons, New York, 1991; pp. 287-326.
6. Kirin, S. I.; Vikić-Topić, D.; Meštrović, E.; Kaitner, B.; Eckert-Maksić, M.; J. Organomet. Chem. 1998, 566, 85-91.
7. Dubac, J.; Laporterie, A.; Manuel, G.; Chem. Rev. 1990, 90, 215-263.
8. (a) Eckert-Maksić, M.; In Theoretical Models of Chemical Bonding; Maksić, Z. B., (Ed.); Part 3, Springer-Verlag, Berlin, 1991, pp. 153-198.
9. (b) Eckert-Maksić, M.; In Chemistry of Hydroxyl, Ether and Peroxides Group; Patai, S., (Ed.); Suppl. E2, Wiley, 1993; pp. 299-371.
10. (c) Eckert-Maksić, M.; Maksi-mović, Lj.; J. Org. Chem. 1991, 56, 3719-3722.
11. Preparation of dienes 1-2: (a) Braye, E. H.; Hübel, W.; Caplier, I.; J. Am. Chem. Soc. 1961, 83, 4406-4410.
12. (b) Barton, T. J.; Gottsman, E. E.; Synth. Inorg. Met.-Org. Chem. 1973, 3, 201-204.
13. (c) Kirin, S. I.; Ph.D. Thesis, University of Zagreb, 1998.
14. Preparation of dienophiles 3-6: (a) Sasaki, T.; Kanematsu, K.; Hayakawa K.; Uchide, M.; J. Chem. Soc., Perkin Trans. I 1972, 2750-2755.
15. (b) Maksimović, Lj.; Novak, N.; Eckert-Maksić, M.; Synth. Commun. 1993, 23, 3119-3125.
16. 3) δ/ppm: -7.18, -3.00, 29.84, 52.72, 54.15, 54.76, 79.03, 82.02, 124.82, 125.28, 126.90, 127.86, 129.01, 130.52, 138.76, 138.85, 141.78; MS (EI, -20 eV) m/z: 579 (M+H, 100).
17. Kirin, S. I.; Eckert-Maksić, M.; unpublished results.