The 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Coupling of Norbornenes and 7-Oxanorbornenes under High Pressure: New Structures, Mechanistic Detail and Synthetic Applications

Synlett

Volumn 1997, Issue 2, 1997, Pages 196-198

  Warrener, Ronald N ^a   Margetic, Davor ^a   Tiekink, Edward R T ^b   Russell, Richard A ^c  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

^c DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001987071     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-738     Document Type: Article

References (21)

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7. Warrener, R. N.; Butler, D. N.; Liao, W. Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett., 1991, 32, 1889.
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9. Warrener, R. N.; Margetic, D.; Schultz, A. C.; Butler, D. N.; Mahadevan, I.; Russell, R. A. Angew. Chem., Int. Ed. Engl. 1997, 36, submitted.
10. Drew, M. G. B.; Geoge, A. V.; Isaacs, N. S.; Rzepa, H. S. J. Chem. Soc. Perkin Trans. 1, 1985, 1277.
11. 8
12. In contrast with the thermal reaction, essentially no 2-naphthol byproduct was produced from 6 under these high pressure conditions.
13. 12 on a Silicon Graphics INDIGO R4000 or R4600 workstations. Semiempirical calculations were conducted using the AM1 Hamiltonian. Geometric optimizations were carried out without using symmetry or any other structural restrictions. A vibrational analysis was also performed for all structures. Each transition structure was located using a standard routine within SPARTAN (linear synchronous transit method) and were shown to be maxima on the potential energy surface by the possession of only one imaginary frequency of vibration, corresponding to the motion of forming new C-C bonds for concerted transition structures.
14. SPARTAN v4.1.1, Wavefunction, Inc., California, 1996.
15. C,F=279.08 Hz); 139.80; MS (m/e, %): 149 (48); 67 (27); 55 (50); 44 (100); 41 (54);
16. The structure of 11 has been determined at room temperature: colourless crystals, orthorhombic space group Pbca, a = 14.328(3), b = 23.788(2) and c = 10.730(3) A, Z = 8, R = 0.078 for 684 reflections.
17. Smith, C. D. J. Am. Chem. Soc., 1966, 88, 4273.
18. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1977, 16, 572.
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21. Kalwinsch, I.; Li X.; Gottstein, J.; Huisgen, R. J. Am. Chem. Soc. 1981, 103, 7032.