1,3-Dipolar Cycloaddition Reactions Of 1-Aza-1-Cyclooctene 1Oxide AlJaroudi, SS; Perzanowski, HP; Wazeer, MIM; Ali, SA PERGAMON-ELSEVIER SCIENCE LTD, TETRAHEDRON; pp: 5581-5592; Vol: 53 King Fahd University of Petroleum & Minerals http://www.kfupm.edu.sa Summary The stereochemistry and reactivity of the cycloaddition reactions of eight-membered cyclic nitrone (4) with several alkenes have been studied. The concentrated solution of the cyclic nitrone undergoes polymerization to give acyclic polynitrone (15). The nitrone 4 is found to be less reactive than its seven-membered counterpart. Barrier to nitrogen inversion in one of the cycloaddition product, a 8/5 fused ring system, was determined to be 55.4 kJ/mol. (C) 1997 Elsevier Science Ltd. References: 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. ADAMS DR, 1991, J CHEM SOC CHEM 0915, P1261 ALFORD EJ, 1966, J CHEM SOC C, P11203 ALI SA, 1988, J CHEM SOC P1, P597 ALI SA, 1988, TETRAHEDRON, V44, P187 ALI SA, 1988, TETRAHEDRON, V44, P5911 ALI SA, 1990, TETRAHEDRON, V46, P7207 ALI SA, 1992, J CHEM RES M, P614 ALI SA, 1992, TETRAHEDRON, V48, P5273 ALI SK, 1992, J CHEM RES S, P62 CARRUTHERS W, 1990, J CHEM SOC P1, P2323 CONFALONE PN, 1988, ORG REACTIONS, V36, P1 COX JD, 1963, TETRAHEDRON, V19, P1175 ELIEL EL, 1994, STEREOCHEMISTRY ORGA, CH3 ELSWORTH JF, 1968, J CHEM SOC C, P2423 ENGLERT G, 1961, Z ANAL CHEM, V181, P447 GARBISCH EW, 1965, J AM CHEM SOC, V87, P2932 HARRIS RK, 1963, J CHEM SOC, P197 MURAHASHI SI, 1987, TETRAHEDRON LETT, V28, P2383 ROGERS TMA, 1956, NATURE, V177, P128 SANDSTROM J, 1982, DYNAMIC NMR SPECTROS © Copyright: King Fahd University of Petroleum & Minerals; http://www.kfupm.edu.sa 21. 22. 23. 24. 25. THESING J, 1956, CHEM BER, V89, P2159 TURFARIELLO JJ, 1984, DIPOLAR CYCLOADDITIO, V2, P83 WAZEER MIM, 1993, CAN J APPL SPECTROSC, V38, P22 WAZEER MIM, 1993, J PHYS ORG CHEM, V6, P326 WAZEER MIM, 1993, MAGN RESON CHEM, V31, P12 For pre-prints please write to: abstracts@kfupm.edu.sa © Copyright: King Fahd University of Petroleum & Minerals; http://www.kfupm.edu.sa