Aspects of stereoselectivity in electrophilic addition reactions of iodine with 5-allenyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one and its derivatives

Russian Chemical Bulletin

Volumn 52, Issue 11, 2003, Pages 2483-2489

  Ivanova, N A ^a   Shainurova, A M ^a   Shitikova, O V ^a   Valiullina, Z R ^a   Miftakhov, M S ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Allenes; Iodination; Isomerism

Indexed keywords

CYCLOPENTANE DERIVATIVE; IODINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; MOLECULAR DYNAMICS; STEREOCHEMISTRY;

EID: 3543124138     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUCB.0000012374.85420.ba     Document Type: Article

References (30)

1. T. L. Jacobs, in The Chemistry of Allenes; Ed. S. R. Landor, Academic Press, New York, 1982, 1, 417.
2. W. Smadja, Chem. Rev., 1983, 83, 263.
3. W. L. Waters, W. S. Linn, and M. C. Caserio, J. Am. Chem. Soc., 1968, 90, 6741.
4. G. A. Tolstikov, S. A. Ismailov, and M. S. Miftakhov, Zh. Org. Khim., 1989, 25, 1566 [J. Org. Chem. USSR, 1989, 25, No. 7 (Engl. Transl.)].
5. G. A. Tolstikov, S. A. Ismailov, and M. S. Miftakhov, Zh. Org. Khim., 1989, 25, 1566 [J. Org. Chem. USSR, 1989, 25, No. 7 (Engl. Transl.)].
6. G. A. Tolstikov, S. A. Ismailov, E. V. Prishchepova, and M. S. Miftakhov, Zh. Org. Khim., 1991, 27, 2539 [J. Org. Chem. USSR, 1991, 27, No. 12 (Engl. Transl.)].
7. G. A. Tolstikov, S. A. Ismailov, E. V. Prishchepova, and M. S. Miftakhov, Zh. Org. Khim., 1991, 27, 2539 [J. Org. Chem. USSR, 1991, 27, No. 12 (Engl. Transl.)].
8. M. S. Miftakhov, N. A. Ivanova, S. A. Yumagulova, S. A. Torosyan, and N. S. Vostrikov, Zh. Org. Khim., 1995, 31, 1639 [Russ. J. Org. Chem., 1995, 31 (Engl. Transl.)].
9. M. S. Miftakhov, N. A. Ivanova, S. A. Yumagulova, S. A. Torosyan, and N. S. Vostrikov, Zh. Org. Khim., 1995, 31, 1639 [Russ. J. Org. Chem., 1995, 31 (Engl. Transl.)].
10. R. R. Akhmetvaleev, L. R. Imaeva, T. A. Belogaeva, and M. S. Miftakhov, Izv. Akad. Nauk, Ser. Khim., 1997, 1699 [Russ. Chem. Bull., 1997, 46, 1622 (Engl. Transl.)].
11. R. R. Akhmetvaleev, L. R. Imaeva, T. A. Belogaeva, and M. S. Miftakhov, Izv. Akad. Nauk, Ser. Khim., 1997, 1699 [Russ. Chem. Bull., 1997, 46, 1622 (Engl. Transl.)].
12. G. A. Tolstikov, R. M. Khalikov, S. A. Ismailov, R. R. Akhmetvaleev, and M. S. Miftakhov, Zh. Org. Khim., 1993, 29, 342 [Russ. J. Org. Chem., 1993, 29, No. 2 (Engl. Transl.)].
13. G. A. Tolstikov, R. M. Khalikov, S. A. Ismailov, R. R. Akhmetvaleev, and M. S. Miftakhov, Zh. Org. Khim., 1993, 29, 342 [Russ. J. Org. Chem., 1993, 29, No. 2 (Engl. Transl.)].
14. R. R. Akhmetvaleev, L. R. Imaeva, and M. S. Miftakhov, Zh. Org. Khim., 1997, 33, 1342 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].
15. R. R. Akhmetvaleev, L. R. Imaeva, and M. S. Miftakhov, Zh. Org. Khim., 1997, 33, 1342 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].
16. T. Pretch, J. Clerc, W. Seibl, and K. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, London - Paris - Tokyo - Hong Kong, 1983, p. H215.
17. J. K. Whitesele and M. A. Minton, J. Am. Chem. Soc., 1987, 109, 225.
18. F. W. Wenrli and T. Nishida, in The Chemistry of Organic Natural Products, Eds. W. Herz, H. Grisebach, and G. W. Kirby, Springer Verlag, New York, 1979, p. 1.
19. B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov, YaMR-spektroskopiya v organicheskoi khimii [NMR Spectroscopy in Organic Chemistry], Khimiya, Leningrad, 1983, 162 (in Russian).
20. N. S. Vostrikov, V. V. Vasikov, L. V. Spirikhin, and M. S. Miftakhov, Zh. Org. Khim., 2001, 37, 1403 [Russ. J. Org. Chem., 2001, 37 (Engl. Transl.)].
21. N. S. Vostrikov, V. V. Vasikov, L. V. Spirikhin, and M. S. Miftakhov, Zh. Org. Khim., 2001, 37, 1403 [Russ. J. Org. Chem., 2001, 37 (Engl. Transl.)].
22. D. J. Pasto, Tetrahedron, 1984, 40, 2813.
23. W. Runge, in The Chemistry of Allenes, Ed. S. R. Landor, Academic Press, New York, 1982, 1, 417.
24. M. C. Findlay, W. L. Waters, and M. C. Caserio, J. Org. Chem., 1971, 36, 278.
25. D. Jarratt, P. L. Beanien, and M. D. Ryan, Tetrahedron, 1980, 36, 1507.
26. Z. Rappoport and Y. Apeloig, J. Am. Chem. Soc., 1969, 91, 6734.
27. J. March, Advanced Organic Chemistry, J. Wiley and Sons, New York, 1985, 1, 337.
28. G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
29. A. Krief and A. M. Laval, Chem. Rev., 1999, 99, 745.
30. J. G. Kirchner, Thin-Layer Chromatography, John Wiley and Sons, New York, 1978, 1, 228.