The reaction of mono-aryl substituted methylenecyclobutanes with diphenyl diselenide in the presence of iodosobenzene diacetate and H2O

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 798-801

  Jiang, Min ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl (1 phenylselanylcyclobutyl)methanones; Diphenyl diselenide; Iodobenzene diacetate; Mono aryl substituted methylenecyclobutanes

Indexed keywords

2 CHLOROPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; 3 BROMOPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; 3 CHLOROPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]ETHANONE; 4 BROMOPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; 4 CHLOROPHENYL(1 (PHENYLSELANYL)CYCLOBUTYL)METHANONE; 4 ETHYLPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; 4 FLUOROPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; 4 NITROPHENYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; CYCLOBUTANE DERIVATIVE; DIPHENYL DISELENIDE; IODOSOBENZENE; M TOLYL[1 (PHENYLSELANYL)CYCLOBUTYL]METHANONE; OXYGEN 18; P TOLYL[1 (PHENYLSELANYL)CYCLOBUTYL]ETHANONE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 57649102719     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.052     Document Type: Article

References (34)

1. Nogueira C.W., Zeni G., and Rocha J.B.T. Chem. Rev. 104 (2004) 6255-6286
2. Mugesh G., du Mont W.W., and Sies H. Chem. Rev. 101 (2001) 2125-2180
3. Parnham M.J., and Graf E. Prog. Drug Res. 36 (1991) 9-11
4. Nogueira C.W., Quinhones E.B., Jung E.A.C., Zeni G., and Rocha J.B.T. Inflamm. Res. 52 (2003) 56-59
5. Huguet J.L. Adv. Chem. Ser. (1967) 345-349
6. Sharpless K.B., Young M.W., and Lauer R.F. Tetrahedron Lett. 22 (1973) 1979-1982
7. Reich H.J. J. Org. Chem. 40 (1975) 2570-2572
8. Sharpless K.B., and Lauer R.F. J. Am. Chem. Soc. 94 (1972) 7154-7155
9. Nicolaou K.C., and Petasis N.A. Selenium in Natural Products Synthesis (1984), CIS, Philadelphia
10. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis (1986), Pergamon, Oxford
11. Patai S., and Rappoport Z. The Chemistry of Organic Selenium and Tellurium Compounds Vol. 1 (1986), Wiley, New York, NY
12. Liotta D. Organoselenium Chemistry (1987), Wiley, New York, NY
13. Krief A., and Hevesi L. Organoselenium Chemistry I (1988), Springer, Berlin
14. Back T.G. Organoselenium Chemistry: A Practical Approach (1999), Oxford University Press, Oxford
15. Reich H.J. Acc. Chem. Res. 12 (1979) 22-30
16. Liotta D. Acc. Chem. Res. 17 (1984) 28-34
17. Wirth T. Topics in Current Chemistry Vol. 208 (2000), Springer, Heidelberg
18. Mugesh G., and Singh H.B. Acc. Chem. Res. 35 (2002) 226-236
19. Shi M., Wang B.-Y., and Li J. Eur. J. Org. Chem. (2005) 759-765
20. Shi M., and Lu J.-M. Synlett (2005) 2352-2356
21. For the synthesis of MCBs, see:. Brandi A., and Goti A. Chem. Rev. 98 (1998) 589-636
22. It has been reported that treatment of diphenyl diselenide with iodosobenzene diacetate produces an electrophilic selenenylating agent for double bonds. See:
23. Tingoli M., Tiecco M., Testaferri L., and Temperini A. Synth. Commun. 28 (1998) 1769-1772
24. Tiecco M., Tingoli M., and Testaferri L. Pure Appl. Chem. 65 (1993) 715-722 and references cited therein
25. Miyoshi N., Takai Y., Murai S., and Sonoda N. Bull. Chem. Soc. Jpn. 51 (1978) 1265-1266
26. Brugier D., Outurquin F., and Paulmier C. J. Chem. Soc., Perkin Trans. 1 (2001) 37-43
27. Reich H.J., Renga J.M., and Reich I.L. J. Am. Chem. Soc. 97 (1975) 5434-5449
28. Chen D.-W., and Chen Z.-C. Tetrahedron Lett. 41 (1994) 7637-7638
29. The examples of water as nucleophilic reagent:
30. Kurz J.L., and Lu J.Y. J. Phys. Chem. 87 (1983) 1444-1448
31. Chi D.Y., Kim D.W., Hong D.J., and Kim H.S. J. Org. Chem. 69 (2004) 3186-3189
32. The oxidation of iodobenzene diacetate:
33. Swenton J.S., Callinan A., Chen Y., Rohde J.J., Kerns M.L., and Morrow J.W. J. Org. Chem. 61 (1996) 1267-1274
34. Canesi S., Bouchu D., and Ciufolini M.A. Org. Lett. 7 (2005) 175-177