Synthesis and Diels-Alder cycloaddition reactions of [(2,2-dichloro-1- fluoroethenyl)sulfinyl] benzene and [(2-chloro-1,2-difluoro ethenyl)sulfinyl] benzene

Tetrahedron

Volumn 56, Issue 22, 2000, Pages 3539-3545

  Sridhar, Madabhushi ^a   Leela Krishna, K ^a   Madhusudana Rao, Jampani ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Diels Alder cycloaddition reaction; Fluorovinyl; Vinylphenyl sulfoxides

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; MICROWAVE IRRADIATION; PHOTOACTIVATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0342657033     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00242-8     Document Type: Article

References (26)

1. Kappe O.C., Murphree S.S., Padwa A. Tetrahedron. 53:1997;14179.
2. Leroy J., Molines H., Wakselman C. J. Org. Chem. 52:1987;290.
3. (a) Crowley, P. J.; Percy. J. M.; Stansfield, K. Chem. Commun. 1997, 21, 2033.
4. (b) Crowley, P. J.; Percy. J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 8233.
5. (c) Baum, K.; Archibald, T. G.; Tzeng, D.; Gilardi, R.; Flippen-Anderson, J. L.; George, C. J. Org. Chem. 1991, 56, 537.
6. (a) Paquette, L. A.; Moerck, R. E.; Harirchain, B.; Magnus, P. D. J. Am. Chem. Soc. 1978, 100, 1597.
7. (b) Paquette, L. A.; Richard, W. V.; Carr, R. V. C.; Charumilind, P.; Blount, J. F. J. Org. Chem. 1982, 47, 4566.
8. Carretero C.J., Garcio Ruano L.J., Martin Cabrejas M.L. Tetrahedron: Asymmetry. 8:1997;2215.
9. Guessous. A.; Rouessac, F.; Maignan. C. Bull. Soc. Chem. Fr. 1986, 837.
10. (b) Brimble. M. A.; Davis. B. R. Tetrahedron 1985, 41, 4965.
11. (c) De Lucchi, O.; Buso, H.; Modena. G. Tetrahedron Lett. 1987, 28, 107.
12. (d) Maignan. C.; Guessous, A.; Rouessac, F. Tetrahedron Lett. 1984, 25, 1727.
13. Fuji K., Tanaka K., Abe H., Matsumoto K., Harayama T., Ikeda A., Taga T., Miwa Y., Node M. J. Org. Chem. 59:1994;2211.
14. (a) Lopez, R.; Carretero, J. C. Tetrahedron: Asymmetry 1991, 2, 93.
15. (b) De Lucchi, O.; Lucchini. V.; Marchioro, C.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457.
16. Knunyants I.L., Fokin A.V. Izvest. Akad. Nauk. SSSR. 1952;261. [CA 47: 3221c].
17. 4b is determined to be a mixture of its geometrical isomers in the ratio 2:3. Its oxidation product 5b, however could not give good resolution in GC analyses and hence we could not obtain the ratio of its geometrical isomers.
18. Sridhar M., Leela Krishna K., Srinivas K., Madhusudana Rao J. Tetrahedron Lett. 39:1998;6529.
19. Adducts 10, 14 and 15 are expected to be mixtures of their diastereomers. These, however, remained unresolvable by thin layer chromatography.
20. De Tollenaere C., Ghosez L. Tetrahedron. 53:1997;17127-17138.
21. In the case of cycloaddition of 5a and its corresponding sulfone 6a with cyclopentadiene, the cycloadduct obtained with each of these dienophiles is a mixture of exo and endo diastereomers. However endo phenyl sulfoxide is major in 5a while exo phenylsulfone is major in 6a (our unpublished results).
22. Birchall J.M., Haszeldine R.N., Parkinson A.R. J. Chem. Soc. 1961;2204.
23. Okuhara K. J. Org. Chem. 43:1978;2745.
24. Li X., Pen H., Jiang X. Huaxue Xuebo. 42:1984;297. [CA 101: 54178m].
25. Hudlicky M. Chemistry of Organofluorine Compounds. 2nd ed. 1992;722 Ellis Horwood, Chichester.
26. Yagulposkii L.M., Aleksandrov A.M. Zh. Obsch. Khim. SSSR. 39:1969;765. [CA 71: 60927h].