Easy availability of more concentrated and versatile dimethyldioxirane solutions

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3585-3586

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

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; REAGENT;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS;

EID: 0029978637     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00628-4     Document Type: Article

References (11)

1. For reviews on dioxiranes see: a) Curci, R., Dinoi, A., Rubino, M.F. Pure & Appl. Chem. 1995, 67, 811-822.
2. b) Murray, R. W., Chem. Rev. 1989, 89, 1187-1201.
3. Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115.
4. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
5. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
6. Singh, M.; Murray, R. W. J. Org. Chem. 1992, 57, 4263-4270.
7. Adam, W.; Curci, R.; Gonzalez, N. M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654-7658.
8. 2.
9. If convenient, the DMD remaining in the aqueous phase could be almost quantitatively recovered by reextraction.
10. 4 (1 ml). The results obtained for the 3 successive extracts carried out, expressed as molar concentration of TFMD, % TFMD recovery and molar concentration of the remaining TFA were, respectively: i) 1.44, 27%, 2.18; ii) 0.29, 7%, 0.22; iii) 0.05, 1%, 0.15. As shown, the first extract was highly concentrated in TFMD although with low recovery yields; also interesting, most of the initial TFA could be removed at the same time, 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., reactions in NMR tubes.
11. Financial support from CICYT-Generalitat de Catalunya (Grant QFN-92-4304) and a fellowship from "Direccio General d'Universitats" to one of us (M.G.) are acknowledged.