Epoxidation by dimethyldioxirane: Kinetics for cis-alkenes

Heterocyclic Communications

Volumn 3, Issue 5, 1997, Pages 393-396

  Baumstark, A L ^a   Michelena Baez, Elba ^a   Navarro, Angela M ^a   Banks, Harold D ^b  

^a GEORGIA STATE UNIVERSITY   (United States)

^b U S ARMY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031327786     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1997.3.5.393     Document Type: Article

References (14)

1. For reviews see: a) R. Curci in "Advances in Oxygenated Processes" Vol. 2; A.L. Baumstark, Ed., JAI Press, Greenwich, CT 1990 b) W. Adam, L.P. Hadjiarapoglou, R. Curci, R. Mello, chapt. 4 in "Organic Peroxides," W. Ando, Ed., Wiley and Sons: Chichester, England 1992 c) W. Adam, L.P. Hadjiarapoglou, Top. Curr. Chem. 164, 45 (1993) d) R. Curci, A. Dinoi, M.F. Rubino, Pure Appl. Chem. 67, 811 (1995).
2. For reviews see: a) R. Curci in "Advances in Oxygenated Processes" Vol. 2; A.L. Baumstark, Ed., JAI Press, Greenwich, CT 1990 b) W. Adam, L.P. Hadjiarapoglou, R. Curci, R. Mello, chapt. 4 in "Organic Peroxides," W. Ando, Ed., Wiley and Sons: Chichester, England 1992 c) W. Adam, L.P. Hadjiarapoglou, Top. Curr. Chem. 164, 45 (1993) d) R. Curci, A. Dinoi, M.F. Rubino, Pure Appl. Chem. 67, 811 (1995).
3. For reviews see: a) R. Curci in "Advances in Oxygenated Processes" Vol. 2; A.L. Baumstark, Ed., JAI Press, Greenwich, CT 1990 b) W. Adam, L.P. Hadjiarapoglou, R. Curci, R. Mello, chapt. 4 in "Organic Peroxides," W. Ando, Ed., Wiley and Sons: Chichester, England 1992 c) W. Adam, L.P. Hadjiarapoglou, Top. Curr. Chem. 164, 45 (1993) d) R. Curci, A. Dinoi, M.F. Rubino, Pure Appl. Chem. 67, 811 (1995).
4. For reviews see: a) R. Curci in "Advances in Oxygenated Processes" Vol. 2; A.L. Baumstark, Ed., JAI Press, Greenwich, CT 1990 b) W. Adam, L.P. Hadjiarapoglou, R. Curci, R. Mello, chapt. 4 in "Organic Peroxides," W. Ando, Ed., Wiley and Sons: Chichester, England 1992 c) W. Adam, L.P. Hadjiarapoglou, Top. Curr. Chem. 164, 45 (1993) d) R. Curci, A. Dinoi, M.F. Rubino, Pure Appl. Chem. 67, 811 (1995).
5. Selected publications: a) Y. Angelis, X. Zhang and M. Orfanopoulos, Tet. Letters, 5991 (1996) b) A.L. Baumstark and D.B. Harden, J. Org. Chem. 58, 7615 (1990) c) R.W. Murray and D.L. Shiang, J. Chem. Soc. Perkin Trans 2, 349 (1990) d) A.L. Baumstark and C.J. McCloskey, Tet. Letters, 3311 (1987).
6. Selected publications: a) Y. Angelis, X. Zhang and M. Orfanopoulos, Tet. Letters, 5991 (1996) b) A.L. Baumstark and D.B. Harden, J. Org. Chem. 58, 7615 (1990) c) R.W. Murray and D.L. Shiang, J. Chem. Soc. Perkin Trans 2, 349 (1990) d) A.L. Baumstark and C.J. McCloskey, Tet. Letters, 3311 (1987).
7. Selected publications: a) Y. Angelis, X. Zhang and M. Orfanopoulos, Tet. Letters, 5991 (1996) b) A.L. Baumstark and D.B. Harden, J. Org. Chem. 58, 7615 (1990) c) R.W. Murray and D.L. Shiang, J. Chem. Soc. Perkin Trans 2, 349 (1990) d) A.L. Baumstark and C.J. McCloskey, Tet. Letters, 3311 (1987).
8. Selected publications: a) Y. Angelis, X. Zhang and M. Orfanopoulos, Tet. Letters, 5991 (1996) b) A.L. Baumstark and D.B. Harden, J. Org. Chem. 58, 7615 (1990) c) R.W. Murray and D.L. Shiang, J. Chem. Soc. Perkin Trans 2, 349 (1990) d) A.L. Baumstark and C.J. McCloskey, Tet. Letters, 3311 (1987).
9. 2b,d that was an adaptation of the experimental approach of a) R.W. Murray and R.J. Jeyaraman, J. Org. Chem., 50, 2847 (1985) b) also see W. Adam, L. Hadjiarapoglou, and J. Bialas, Chem. Ber., 124, 2377 (1991).
10. 2b,d that was an adaptation of the experimental approach of a) R.W. Murray and R.J. Jeyaraman, J. Org. Chem., 50, 2847 (1985) b) also see W. Adam, L. Hadjiarapoglou, and J. Bialas, Chem. Ber., 124, 2377 (1991).
11. A.L. Baumstark and P.C. Vasquez, J. Org. Chem. 53, 3437 (1988).
12. R.D. Bach, J.L Andrés, A.L. Owensby, H.B. Schlegel and J.J.W. McDouall, J. Am. Chem. Soc. 114, 7207 (1992).
13. Calculations were performed on a Silicon Graphics Indigo 2 workstation using Spartan version 3.1 (Wavefunction, Inc.). Transition state determination was judged successful when the calculated structure possessed a single imaginary frequency that when animated illustrated that it was on the reaction coordinate.
14. E.L. Eliel and S.H. Wilen, Stereochemistry of Organic Compounds; Wiley-Interscience, New York 1994, pp. 647-651.