Ru(III) catalyses the conversion of epoxides to 1,3-dioxolanes

Synthetic Communications

Volumn 28, Issue 17, 1998, Pages 3189-3193

  Iranpoor, N ^a   Kazemi, F ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ACETONE; CARBOHYDRATE; EPOXIDE; STEROID;

ARTICLE; CATALYSIS; DATA ANALYSIS; INFRARED SPECTROMETRY; ISOLATION PROCEDURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0031904344     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004420     Document Type: Article

References (13)

1. Green, T. H., Wuts, P. G. M., "Protective Groups in Organic Synthesis," 2nd ed., John Wiley, New York, 1991, pp188-195.
2. F. A. J. Meskens, Synthesis 1981, 501.
3. Due to the stability of the dioxolane ring, they are used instead of the corresponding epoxides and diols for mass spectrometry, Hanzlik, R. P. and Leinwetter, M., J. Org. Chem., 1978, 43, 438.
4. (a) H. Steinbrink, German Patent (DOS) 1086241, Chemische Werke Huls AG, 1959; C. A., 1962, 56, 5969.
5. (b) A.A. Gevorkyan, P. I. Kazaryan, O. V. Avakyan, and R. A. Vardanyan, Khim. Geterotsikl. Soedin. 1991, 1, 33; C. A., 1991, 115, 8633x.
6. (b) A.A. Gevorkyan, P. I. Kazaryan, O. V. Avakyan, and R. A. Vardanyan, Khim. Geterotsikl. Soedin. 1991, 1, 33; C. A., 1991, 115, 8633x.
7. 5b have been reported to give rearranged products .(a) B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc., 1971, 93, 1693.
8. (b) P. F. Hudrlik, R. N. Misra, G. P. Withers, H. M. Hudrlik, R. J. Rona and J. P. Arcoleo, Tetrahedron Lett., 1976, 1453.
9. 6b give the corresponding halohydrins (a) J. Kagan, B. E. Firth, N. Y. Shih, and C. Boyajian, J. Org. Chem., 1977, 42, 343.
10. (b) D. J. Harvey, Res. Commun. Chem. Pathol. Parmacol., 1972, 4, 247.
11. The reaction has been reported not to go to completion and also failed with epoxides caring electron releasing groups. D. S. Torok, J. J. Figueroa, and W. J. Scott, J. Org. Chem., 1993, 58, 7274.
12. 4 has been observed to produce little or no product
13. N. Iranpoor, F. Kazemi, Tetrahedron, 1997, in press.