Ab initio studies of the allylic hydroxylation: DFT calculation on the reaction of 2-methyl-2-butene with selenium dioxide

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 1099-1102

  Ra, Choon Sup ^a   Park, Gyoosoon ^b  

^a Yeungnam University   (South Korea)

^b Kookmin University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 2 BUTENE; ALKENE DERIVATIVE; ALLYL ALCOHOL; METHYL GROUP; SELENIUM DERIVATIVE; SELENIUM OXIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; HYDROXYLATION; QUANTUM MECHANICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037467823     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02715-6     Document Type: Article

References (20)

1. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
2. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
3. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
4. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
5. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
6. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
7. For reviews, see: (a) Bulman Page, P. C.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p. 83; (b) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; (c) Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p. 579; (c) Rabjohn, N. Org. React. 1978, 24, 261; (d) Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279; (e) Rabjohn, N. Org. React. 1949, 5, 331; (f) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
8. Examples for the synthetic applications, see: (a) Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205; (b) Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979; (c) Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704; (d) Madec, D.; Ferezou, J. P. Synlett 1996, 867; (e) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
9. Examples for the synthetic applications, see: (a) Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205; (b) Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979; (c) Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704; (d) Madec, D.; Ferezou, J. P. Synlett 1996, 867; (e) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
10. Examples for the synthetic applications, see: (a) Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205; (b) Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979; (c) Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704; (d) Madec, D.; Ferezou, J. P. Synlett 1996, 867; (e) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
11. Examples for the synthetic applications, see: (a) Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205; (b) Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979; (c) Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704; (d) Madec, D.; Ferezou, J. P. Synlett 1996, 867; (e) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
12. Examples for the synthetic applications, see: (a) Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205; (b) Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979; (c) Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704; (d) Madec, D.; Ferezou, J. P. Synlett 1996, 867; (e) Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
13. Sharpless K.B., Lauer R.F. J. Am. Chem. Soc. 94:1972;7154.
14. Arigoni D., Vasella A., Sharpless K.B., Jensen H.P. J. Am. Chem. Soc. 95:1973;7917.
15. Singleton D.A., Hang C. J. Org. Chem. 65:2000;7554.
16. Gaussian 98, Revision A.7, Frisch, M. J. et al., Gaussian, Inc., Pittsburgh, PA, 1998.
17. For calculations of the transition states of the ene reaction at B3LYP/6-311+G(d,p) level of theory, see Ref. 4.
18. Density Functional Methods in Chemistry; Labanowski, J. K., Andzelm, J. W., Eds.; Springer-Verlag: New York, 1991.
19. Parr R.G., Yang W.T. Annu. Rev. Phys. Chem. 46:1995;701.
20. 10; -2748.558624 for TS1-1(anti-endo); -2748.554039 for TS1-2(anti-exo); -2748.557407 for TS1-3(syn-endo); -2748.554821 for TS1-4(syn-exo); -2748.552171 for TS1-5(terminal-endo); -2748.551968 for TS1-6(terminal-exo); -2748.566324 for TS2-1-a; -2748.561602 for TS2-1-b; -2748.562080 for TS2-3-a; -2748.565643 for TS2-3-b.