Synthesis And Cycloaddition Reactions Of 2,3,4,5Tetrahydropyrazine 1-Oxide Wazeer, MIM; Perzanowski, HP; Qureshi, SI; Al-Murad, MB; Ali, SA PERGAMON-ELSEVIER SCIENCE LTD, TETRAHEDRON; pp: 7229-7236; Vol: 56 King Fahd University of Petroleum & Minerals http://www.kfupm.edu.sa Summary The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine I-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined. (C) 2000 Elsevier Science Ltd. ALI rights reserved. References: 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. © *DAR LAB SCI ENG R, NMR PROGR LIB ALFORD EJ, 1966, J CHEM SOC C, P1103 ALI SA, 1988, J CHEM SOC P1, P597 ALI SA, 1988, TETRAHEDRON, V44, P187 ALI SA, 1988, TETRAHEDRON, V44, P5911 ALI SA, 1992, J CHEM RES M, P614 ALI SA, 1992, TETRAHEDRON, V48, P5273 ALI SA, 1998, J CHEM SOC PERK DEC, P2699 ALI SK, 1992, J CHEM RES S, P62 ALJAROUDI SS, 1997, TETRAHEDRON, V53, P5581 COFALONE PN, 1988, ORG REACTIONS, V36, P1 ELIEL EL, 1965, CONFORMATION ANAL IN, CH4 ELSWORTH JF, 1968, J CHEM SOC C, P2423 INGOLD C, 1927, J CHEM SOC 2, P2918 KALINOWSKI H, 1988, CARBON 13 NMR SPECTR MURAHASHI SI, 1987, TETRAHEDRON LETT, V28, P2383 PADWA A, 1984, 1 3 DIPOLAR CYCLOADD, V2, P83 PERRIN CL, 1991, J ORG CHEM, V56, P7034 Copyright: King Fahd University of Petroleum & Minerals; http://www.kfupm.edu.sa 19. 20. 21. 22. 23. 24. 25. RIDDELL FG, 1981, TETRAHEDRON, V37, P849 ROGERS TMA, 1956, NATURE, V177, P128 SANDSTROM J, 1982, DYNAMIC NMR SPECTROS THESING J, 1956, CHEM BER, V89, P2159 TUFARIELLO JJ, 1984, 1 3 DIPOLAR CYCLOADD, V2, P83 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