Observation of secondary 2-butene ozonide in the ozonation of trans-2-butene in the gas phase

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3391-3394

  Fajgar, Radek ^a   Vítek, Josef ^a   Haas, Yehuda ^b   Pola, Josef ^a  

^a INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; REACTION ANALYSIS;

EID: 0043233457     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00554-0     Document Type: Article

References (27)

1. (a) Altshuller, A. P. Atmos. Environ. 1983, 17, 2383.
2. (b) Atkinson, R.; Carter, W. P. L. Chem. Rev. 1984, 84, 437.
3. (c) Grosjean, D. Environ. Sci. Technol. 1990, 24, 1428.
4. (d) Atkinson; Aschmann, R.; S. M. Environ. Sci. Technol. 1993, 27, 1357.
5. Herron, J. T; Martinez, R. I.; Huie, R. E. Int. J. Chem. Kinet. 1982, 14, 20 and refs. therein.
6. (a) Kuczkowski, R. L. Chem. Soc. Rev. 1992, 79.
7. (b) Zvilichowski, G. in The chemistry of hydroxyl, ether and peroxide groups, Vol. 2, Suppl. E, S. Patai, ed., Wiley, New York, 1993.
8. (c) Bailey, P. S. Ozonation in organic chemistry, Academic Press, New York, Vol. I, 1978.
9. (d) Kuczkowski, R. L in 1,3-Dipolar cycloaddition chemistry, A. Padwa, ed., Wiley, New York, Vol. 2, Ch. 11, 1984.
10. (a) Martinez, R. I.; Huie R. E.; Herron, J. T. Chem. Phys. Lett. 1980, 72, 443.
11. (b) Martinez, R. I.; Herron, J. T.; Huie, R. E. J Am. Chem. Soc. 1981, 103, 3807.
12. (c) Martinez, R. I.; Herron, J. J. Phys. Chem. 1988, 92, 4644.
13. (d) Atkinson, R. Finlayson, B. J.; Pitts, J. N. J. Am. Chem. Soc. 1973, 95, 7592.
14. (e) Finlayson, B. J.; Pitts, J. N.; Atkinson, R. J. Am. Chem. Soc. 1974, 96, 5356.
15. Khachatryan, L.; Fajgar, R.; Haas, Y.; Pola, J. J. Chem. Soc., Perkin 2, submitted.
16. Kühne, H.; Foster, M.; Hulliger, J.; Ruprecht, H.; Bauder, A.; Günthard, H-H. Helv. Chim. Acta 1980, 63, 1971.
17. Horie, O.; Moortgat, G. K. Chem. Phys. Lett. 1989, 156, 39.
18. (a) Herron, J. T.; Martinez, R. I.; Huie, R. E. Int. J. Chem. Kinet. 1982, 14, 201.
19. (b) Su, F.; Calvert, J. G.; Shaw, J. H. J. Phys. Chem. 1980, 84, 239.
20. (c) Kan, C. S.; Su, F.; Calvert, J. G.; Shaw, J. H. J. Phys. Chem. 1981, 85, 2359.
21. (d) Niki, H.; Maker, P. D.; Savage, C. M.; Breitenbach, L. P. J. Phys. Chem. 1981, 85, 1024.
22. Niki, H.; Maker, P. D.; Savage C. M.; Breitanbach, L. P. Chem. Phys. Lett. 1977, 46 327.
23. 2, each contained in a 2 1 Pyrex flask, were equilibrated by opening the interposed PTFE stopcock. Both flasks were accommodated in a 15 1 box and immersed in dry ice-ethanol.
24. Gaseous samples were withdrawn by a gas-tight syringe through a septum and analysed by gas chromatography (FID) and gas-chromatography-mass spectrometry on 3.3 m long columns packed with 5 % SE-30 on Chromosorb W and 5% 2,2′-oxydipropionitrile on Chromosorb 6-HP. Responce FID factors were determined: acetaldehyde 0.30, acetic acid 0.24, trans-2-butene 1.00, 2-butene-ozonide 0.12.
25. (a) Gillies, C. W.; Lattimer, R. P.; Kuczkowski, R. L. J. Am. Chem. Soc. 1974, 96, 1536.
26. (b) Castonguay, J.; Bertrand, M.; Carles, J.; Fliszár, S.; Rousseau, Y. Can. J. Chem. 1969, 57, 919.
27. Determined as the ratio of the areas for total ion current peaks.