On the regioselectivity of imidoyl radical cyclisations

European Journal of Organic Chemistry

Volumn , Issue 5, 2000, Pages 707-711

  Nanni, Daniele ^a   Calestani, Gianluca ^b   Leardini, Rino ^a   Zanardi, Giuseppe ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Photolysis; Radical reactions; Rearrangements; Semiempirical calculations; X ray scattering

Indexed keywords

BENZENE DERIVATIVE; CYANIDE; DISULFIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0034005803     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200003)2000:5<707::AID-EJOC707>3.0.CO;2-I     Document Type: Article

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32. Hi processes involving alkyl sulfides have been recently suggested to occur through 9-S-3 transition states (K. F. Ferris, J. A. Franz, C. Sosa, R. J. Bartlett, J. Org. Chem. 1992, 57, 777-778), sulfuranyl radicals are assumed to be true intermediates when electronegative atoms are linked to the sulfur and in intramolecular cyclisations onto diarylsulfide moieties, see: R. Leardini, G. F. Pedulli, A. Tundo, G. Zanardi, J. Chem. Soc., Chem. Commun. 1985, 1390-1391 and references cited therein. See also: J. A. Kampmeier, T. R. Evans, J. Am. Chem. Soc. 1966, 88, 4096-4097; A. L. J. Beckwith, D. R. Boate, J. Chem. Soc., Chem. Commun. 1986, 189-190; J. A. Franz, D. H. Roberts, K. F. Ferris, J. Org. Chem. 1987, 52, 2256-2262.
33. Hi processes involving alkyl sulfides have been recently suggested to occur through 9-S-3 transition states (K. F. Ferris, J. A. Franz, C. Sosa, R. J. Bartlett, J. Org. Chem. 1992, 57, 777-778), sulfuranyl radicals are assumed to be true intermediates when electronegative atoms are linked to the sulfur and in intramolecular cyclisations onto diarylsulfide moieties, see: R. Leardini, G. F. Pedulli, A. Tundo, G. Zanardi, J. Chem. Soc., Chem. Commun. 1985, 1390-1391 and references cited therein. See also: J. A. Kampmeier, T. R. Evans, J. Am. Chem. Soc. 1966, 88, 4096-4097; A. L. J. Beckwith, D. R. Boate, J. Chem. Soc., Chem. Commun. 1986, 189-190; J. A. Franz, D. H. Roberts, K. F. Ferris, J. Org. Chem. 1987, 52, 2256-2262.
34. Hi processes involving alkyl sulfides have been recently suggested to occur through 9-S-3 transition states (K. F. Ferris, J. A. Franz, C. Sosa, R. J. Bartlett, J. Org. Chem. 1992, 57, 777-778), sulfuranyl radicals are assumed to be true intermediates when electronegative atoms are linked to the sulfur and in intramolecular cyclisations onto diarylsulfide moieties, see: R. Leardini, G. F. Pedulli, A. Tundo, G. Zanardi, J. Chem. Soc., Chem. Commun. 1985, 1390-1391 and references cited therein. See also: J. A. Kampmeier, T. R. Evans, J. Am. Chem. Soc. 1966, 88, 4096-4097; A. L. J. Beckwith, D. R. Boate, J. Chem. Soc., Chem. Commun. 1986, 189-190; J. A. Franz, D. H. Roberts, K. F. Ferris, J. Org. Chem. 1987, 52, 2256-2262.
35. Hi processes involving alkyl sulfides have been recently suggested to occur through 9-S-3 transition states (K. F. Ferris, J. A. Franz, C. Sosa, R. J. Bartlett, J. Org. Chem. 1992, 57, 777-778), sulfuranyl radicals are assumed to be true intermediates when electronegative atoms are linked to the sulfur and in intramolecular cyclisations onto diarylsulfide moieties, see: R. Leardini, G. F. Pedulli, A. Tundo, G. Zanardi, J. Chem. Soc., Chem. Commun. 1985, 1390-1391 and references cited therein. See also: J. A. Kampmeier, T. R. Evans, J. Am. Chem. Soc. 1966, 88, 4096-4097; A. L. J. Beckwith, D. R. Boate, J. Chem. Soc., Chem. Commun. 1986, 189-190; J. A. Franz, D. H. Roberts, K. F. Ferris, J. Org. Chem. 1987, 52, 2256-2262.
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38. Figure 1 was obtained with ORTEP-3 for Windows, See: L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565.