Observations on the enforced orthogonality concept for the synthesis of fully hindered biaryls by a tin-free intramolecular radical ipso substitution

Synlett

Volumn , Issue 4, 2000, Pages 475-478

  Bonfand, Eric ^a   Forslund, Linnea ^a   Motherwell, William B ^a   Vázquez, Santiago ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Biaryls; Ipso substitution; Radical reactions; Substituent effects; Titanium trichloride

Indexed keywords

DIAZONIUM COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RADICAL; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034106380     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

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9. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Bringman, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. Stanforth, S. P. Tetrahedron 1998, 54, 263. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon Press: Oxford, 1991, Vol 3, Chapter 2.3.
10. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Bringman, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. Stanforth, S. P. Tetrahedron 1998, 54, 263. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon Press: Oxford, 1991, Vol 3, Chapter 2.3.
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15. The competition ipso versus addition has also been observed in other intramolecular radical [1,5] ipso substitutions. Giraud, L.; Lacote, L.; Renaud, P. Helv. Chim. Acta 1997, 80, 2148.
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19. 3-methyl-2-nitroaniline and 3-methoxy-2-nitroaniline were synthesised by using previously described procedures: Dyall, L. K.; Pausacker, K. H. Aust. J. Chem. 1958, 11, 491. Newman, M. S.; Kannan, R. J. Org. Chem. 1976, 41, 3356.
20. 3-methyl-2-nitroaniline and 3-methoxy-2-nitroaniline were synthesised by using previously described procedures: Dyall, L. K.; Pausacker, K. H. Aust. J. Chem. 1958, 11, 491. Newman, M. S.; Kannan, R. J. Org. Chem. 1976, 41, 3356.
21. Satisfactory analytical (combustion and / or high-resolution mass) and spectral (IR, NMR and MS) data were obtained for all new compounds. Yields refer to purification by flash chromatography on silica gel or crystallisation.
22. The diazotisation of an unprotected sulfonamide gave the corresponding benzotriazole derivative.
23. 17NO (227.31) calcd. C 79.26, H 7.54, N 6.16; found C 78.88, H 7.45, N 6.03.