High pressure-promoted [2+2] cycloaddition reactions of 4-methylphenyl 1,2-propadienyl sulfone with enol ethers

European Journal of Organic Chemistry

Volumn , Issue 5, 2003, Pages 894-897

  Aben, René W M ^a   Braverman, Samuel ^b   Scheeren, Hans W ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

1 Alkoxybuta 1,3 dienes; 3 Alkoxymethylene cyclobutanes; Allenes; Cycloadditions; High pressure chemistry; Regioselectivity

Indexed keywords

4 (TERT BUTOXY) 2 METHYLENE 3 BUTENYL 4 METHYLPHENYLSULFONE; 4 ETHOXY 2 METHYLENE 3 BUTENYL 4 METHYLPHENYLSULFONE; 4 METHYLPHENYL 1,2 PROPADIENYLSULFONE; DIMETHYLAMINE; ETHER DERIVATIVE; N [3 (TERT BUTOXY) 1 [(4 METHYLPHENYLSULFONYL)METHYL]CYCLOBUTYL] N,N DIMETHYLAMINE; N [3 ETHOXY 1 [(4 METHYLPHENYLSULFONYL)METHYL]CYCLOBUTYL] N,N DIMETHYLAMINE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; ISOMERISM; STEREOCHEMISTRY; TECHNIQUE;

EID: 0037338445     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390135     Document Type: Article

References (27)

1. For reviews see: [1a] P. H. Beusker, J. W. Scheeren, in: The chemistry of dienes and polyenes, 2000, vol. 2 (Ed.: Z. Rappoport), John Wiley & Sons, 2000, pp. 331-337.
2. [1b] E. Lee-Ruff, in: Houben-Weyl, Melhoden der Organischen Chemie, Vol. E17e (Ed.: A. E. de Meijere), George Thieme Verlag, Stuttgart, 1997, pp. 190-213.
3. [1c] H. E. Schuster, G. M. Coppola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1984.
4. For recent examples of cycloadditions of electron-rich allenes see: [2a] L. L. Wei, R. P. Hsung, H. Xiong, J. A. Mulder, N. T. Nkansah, Org. Lett. 1999, 1, 2145-2148. [2b] M. Kimura, Y. Horino, Y. Wakamiya, T. Okajima, Y. Tamura, J. Am. Chem. Soc. 1997, 119, 10869-10870. [2c] M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123-8126.
5. For recent examples of cycloadditions of electron-rich allenes see: [2a] L. L. Wei, R. P. Hsung, H. Xiong, J. A. Mulder, N. T. Nkansah, Org. Lett. 1999, 1, 2145-2148. [2b] M. Kimura, Y. Horino, Y. Wakamiya, T. Okajima, Y. Tamura, J. Am. Chem. Soc. 1997, 119, 10869-10870. [2c] M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123-8126.
6. For recent examples of cycloadditions of electron-rich allenes see: [2a] L. L. Wei, R. P. Hsung, H. Xiong, J. A. Mulder, N. T. Nkansah, Org. Lett. 1999, 1, 2145-2148. [2b] M. Kimura, Y. Horino, Y. Wakamiya, T. Okajima, Y. Tamura, J. Am. Chem. Soc. 1997, 119, 10869-10870. [2c] M. Hojo, K. Tomita, Y. Hirohara, A. Hosomi, Tetrahedron Lett. 1993, 34, 8123-8126.
7. For recent examples of cycloadditions of electron-poor allenes see: [3a] M. P. S. Ishar, K. Kumar, S. Kaur, N. K. Girdhar, S. Sachar, A. Marwaha, A. Kapoor, Org. Lett. 2001, 3, 2133-2136. [3b] F. Scheufler, M. E. Maier, Eur. J. Org. Chem. 2000, 3945-3948. [3c] J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter, F-G. Tien, Synlett 1998, 900-901.
8. For recent examples of cycloadditions of electron-poor allenes see: [3a] M. P. S. Ishar, K. Kumar, S. Kaur, N. K. Girdhar, S. Sachar, A. Marwaha, A. Kapoor, Org. Lett. 2001, 3, 2133-2136. [3b] F. Scheufler, M. E. Maier, Eur. J. Org. Chem. 2000, 3945-3948. [3c] J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter, F-G. Tien, Synlett 1998, 900-901.
9. For recent examples of cycloadditions of electron-poor allenes see: [3a] M. P. S. Ishar, K. Kumar, S. Kaur, N. K. Girdhar, S. Sachar, A. Marwaha, A. Kapoor, Org. Lett. 2001, 3, 2133-2136. [3b] F. Scheufler, M. E. Maier, Eur. J. Org. Chem. 2000, 3945-3948. [3c] J. R. Bull, N. S. Desmond-Smith, S. J. Heggie, R. Hunter, F-G. Tien, Synlett 1998, 900-901.
10. C. J. M. Stirling, J. Chem. Soc. 1964, 5856-5862.
11. S. Braverman, H. Mechoulam, Tetrahedron 1974, 30, 3883-3890.
12. A. Padwa, M. Meske, S. S. Murphree, S. H. Watterson, Z. Ni, J. Am. Chem. Soc. 1995, 117, 7071-7080.
13. [7a] A. J. Guilford, R. W. Turner, J. Chem. Soc., Chem. Commun. 1983, 466-467.
14. [7b] K. Hayakawa, H. Nishiyama, K. Kanematsu, J. Org. Chem. 1985, 50, 512-517.
15. [7c] N. P. Pavri, M. L. Trudell, Tetrahedron Lett. 1997, 38, 7993-7996.
16. R. Gomper, D. Lach, Angew. Chem. 1973, 85, 582-583, Angew. Chem. Int. Ed. Engl. 1973, 12.
17. R. Gomper, D. Lach, Angew. Chem. 1973, 85, 582-583, Angew. Chem. Int. Ed. Engl. 1973, 12.
18. B. B. Snider, D. K. Spindell, J. Org. Chem. 1980, 45, 5017-5020.
19. J. von Jouanne, H. Kelm, P. J. Huisgen, J. Am. Soc. 1979, 101, 151-158.
20. R. W. M. Aben, R. de Gelder, J. W. Scheeren, Eur. J. Org. Chem. 2002, 3126-3132.
21. D. J. Pasto, K. D. Sugi, D. E. Alonso, J. Org Chem. 1992, 57, 1146-1150, and references cited therein.
22. [13a] F. Wurche, F.-G. Klärner, in: High pressure Chemistry (Eds.: R. van Eldik, F.-G. Klärner), Wiley-VCH, Weinheim, 2002, chapter 2, pp. 41-96.
23. [13b] F-G. Klärner, B. Krawczyk, V. Ruster. U. K. Deiters, J. Am. Chem. Soc. 1994, 116, 7646-7657.
24. R. W. M. Aben, R. Smit, J. W. Scheeren, J. Org. Chem. 1987, 52, 365-370.
25. R. Taylor, J. Chem. Soc., Perkin Trans. 2 1988, 737-744.
26. A. J. Kresge, D. S. Sagatys, H. L. Chen, J. Am. Chem. Soc. 1977, 99, 7228-7233.
27. L. N. Koikov, M. Han, D. M. Wellman, J. A. Kelly, I. P. Smoliakova, Synth. Comm. 2000, 30, 3451-3464.