Availability and reactivity of concentrated dimethyldioxirane solutions in solvents other than acetone

Tetrahedron

Volumn 53, Issue 25, 1997, Pages 8643-8650

  Gibert, Mariona ^a   Ferrer, Marta ^a   Sänchez Baeza, Francisco ^a   Messeguer, Angel ^a  

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETIC ACID ETHYL ESTER; ACETONE; CARBON TETRACHLORIDE; CHLOROFORM; ORGANIC SOLVENT; REAGENT; SOLVENT; TOLUENE;

ARTICLE; CHEMICAL REACTION; EPOXIDATION; EXTRACTION; KINETICS; PRIORITY JOURNAL;

EID: 0030908605     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00533-4     Document Type: Article

References (18)

1. Dedicated to Prof. Waldemar Adam on occasion of his 60 anniversary.
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3. b) Murray, R. W., Chem. Rev. 1989, 89, 1187-1201;
4. c) Adam, W., Curci, R., Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211.
5. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
6. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
7. Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263-70.
8. Ferrer, M.; Sanchez-Baeza, F.; Casas, J.; Messeguer, A. Tetrahedron Lett. 1994, 35, 2981-2984.
9. Cerré, C.; Hofmann, A. F.; Schteingart, C. D.; Jia, W.; Maltby, D. Tetrahedron 1997, 53, 435-446.
10. Ferrer, M.; Gibert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron Lett. 1996, 37, 3585-3586.
11. 2.
12. 4 portions. The results obtained for the three successive extracts, expressed as molar concentration of TFMD, percentage of TFMD recovery and molar concentration of the remaining TFA, were: i) 1.44, 27%, 2.18; ii) 0.29, 7%, 0.22; iii) 0.05, 1%, 0.15, respectively. Thus, the first extract was highly concentrated in TFMD although with low recovery yields; also interesting, most of the initial TFA could be removed concomitantly, which was not the case for the DMD extractions. This procedure, which is susceptible of optimization, could be particularly useful for specific studies, i.a., reaction monitoring in NMR tubes.
13. 13C NMR: δ 101.2, 22.8 ppm.
14. Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437-9.
15. Baumstark, A. L.; Harden, D. B. J. J. Org. Chem. 1993, 58, 7615-7618.
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17. Murray, R. W.; Gu, D. J. Chem. Soc., Perkin Trans 2 1993, 2, 2203-2207.
18. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press, 2nd Ed.: Oxford, 1980.