Hypervalent iodine-induced multi-component reactions: Novel thiocyano- and isothiocyano-phenylselenenylating reaction of alkenes

European Journal of Organic Chemistry

Volumn , Issue 10, 2000, Pages 1865-1870

  Margarita, Roberto ^a   Mercanti, Chiara ^a   Parlanti, Luca ^a   Piancatelli, Giovanni ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Alkenes; Iodine; Isothiocyanates; Selenium; Sulfur; Thiocyanates

Indexed keywords

ALKENE; ISOTHIOCYANIC ACID DERIVATIVE; THIOCYANIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034049957     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200005)2000:10<1865::aid-ejoc1865>3.0.co;2-i     Document Type: Article

References (41)

1. V. V. Zhdankin, R. Tykwinski,. B. L. Williamson, P. J. Stang, N. S. Zefirov, Tetrahedron Lett. 1991, 32, 733-734.
2. P. Magnus, J. Lacour, P. A. Evans, M. B. Roe, C. Hulme, J. Am. Chem. Soc. 1996, 118, 3406-3418 and references therein.
3. A. Varvoglis Tetrahedron 1997, 53, 1179-1255.
4. P. A. Evans, T. A. Brandt, Tetrahedron Lett. 1996, 37, 6443-6446.
5. P. A. Evans, T. A. Brandt, J. Org. Chem. 1997, 62, 5321-5326.
6. A. De Mico, R. Margarita, L. Parlanti, G. Piancatelli, A. Vescovi. J. Org. Chem. 1997, 62, 6974-6977.
7. M. Bruno, R. Margarita, L. Parlanti, G. Piancatelli, M. Trifoni, Tetrahedron Lett. 1998, 39, 3847-3848.
8. A recent report: F. D. Toste, F. Laronde, W. I. Still, Tetrahedron Lett. 1995, 36, 2949-2952.
9. Reviews: [8a] J. L. Wood, Organic Reactions (Ed.: R. Adams), John Wiley & Sons, New York, 1946, Vol. 3, Chapter 6.
10. R. G. Guy, in The Chemistry of Cyanates and Their Thio Derivatives (Ed.: S. Patai), John Wiley & Sons, New York, 1977, Part 2, Chapter 18.
11. Y. Kita, T. Takada, S. Mihara, B. A. Whelan, H. Tohma, J. Org. Chem. 1995, 60, 7144-7148.
12. A. De Mico, R. Margarita, A. Mariani, G. Piancatelli, Chem. Commun. 1997, 1237-1238.
13. The formation of [bis(thiocyano)iodo]benzene A (Equation 1) by reaction between [bis(chloro)iodo]benzene and lead(II) thiocyanate has been reported. The compound was described to be unstable and it was used for the introduction of the thiocyanate group to the para-position of activated aromatic substrates.
14. R. Neu, Chem. Ber. 1939, 72, 1505-1512.
15. Y. Kita, T. Okuno, M. Egi, K. Iio, Y. Takeda, S. Akai, Synlett 1994, 1039-1040.
16. M. Bella, R. Margarita, C. Orlando, M. Orsini, L. Parlanti, G. Piancatelli, Tetrahedron Lett. 2000, 41, 561-565, and references therein.
17. C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis. Pergamon Press, Oxford, 1986, 25-57.
18. W. J. E. Parr, R. C. Crafts, Tetrahedron Lett. 1981, 22, 1371-1732 and references therein.
19. A. Toshimitsu, S. Uemura, M. Okano, J. Org. Chem. 1983, 48, 5246-5251 and references therein.
20. E. M. Stocking, J. N. Schwarz, H. Senn, M. Salzmann, L. A. Silks, J. Chem. Soc., Perkin Trans, 1 1997, 2443-2447.
21. C. Bosman, A. D'Annibale, S. Resta, C. Trogolo, Tetrahedron Lett. 1994, 35, 6525-6528 and references therein.
22. D. G. Garratt, Can. J. Chem. 1979, 57, 2180-2190.
23. D. G. Garratt, M. D. Ryan, M. Ujjainwalla, Can. J .Chem. 1979, 57, 2145-2153.
24. O. Foss, J. Am. Chem. Soc. 1947, 69, 2236-2237.
25. M. Tingoli, M. Tiecco, D. Chianelli, R. Balducci, A. Temperini, J. Org. Chem. 1991, 56, 6809-6813.
26. T. Di Giambernardino, W. Dumont, A. Krief, Tetrahedron Lett. 1983, 24, 3413-3416.
27. P. Buhlmann, S. Nishizawa, K. P. Xiao, Y. Umezawa, Tetrahedron 1997, 53, 1647-1654.
28. J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1996, 35, 1090-1093.
29. S. Nishizawa, P. Buhlmann, M. Iwao, Y. Umezawa, Tetrahedron Lett. 1995, 36, 6483-6486.
30. J. Scheerder, M. C. Fochi, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 7815-7820.
31. E. Fan, S. A. van Arman, S. Kincaid, A. D. Hamilton, J. Am. Chem. Soc. 1993, 115, 369-370.
32. R. N. Atkinson, K. Ichimori, J. D. Stuehr, B. S. King, 216th ACS National Meeting, Book of Abstracts 1998, medi 026.
33. A. W. Erian, S. H. Sherif, Tetrahedron 1999, 55, 7957-8024.
34. J. V. Comasseto, L. W. Ling, N. Petragnani, H. A. Stefani Synthesis 1997, 373-403.
35. H. Tajima, G. Li, Synlett. 1997, 773-774.
36. A. Kjear, A. Schuster, Phytochemistry 1971, 10, 3155-3160.
37. N. Gaind, K. S. Gandhi, T. R. Juneja, A. Kjear, B. J. Nielsen, Phytochemistry 1975, 14, 1415-1418.
38. P. J. Delaquis, G. Mazza, Food Technology 1975, 73.
39. H. M. Mesheram, S. Dale, J. J. Yadav, Tetrahedron Lett. 1997, 38, 8743-8744.
40. J. T. Arnold, B. P. Wilkinson, S. Sharma, V. E. Steele, Cancer Res. 1995, 537.
41. E. Lieber, R. Slutkin, J .Org. Chem. 1962, 27, 2214-2217.