Steric and electronic effects in the synthesis of biaryls and their heterocyclic congeners using intramolecular free radical [1,5] ipso substitution reactions

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 137-140

  Da Mata, Maria Lucília E N ^a   Motherwell, William B ^a   Ujjainwalla, Feroze ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; FURAN DERIVATIVE; IMIDAZOLE DERIVATIVE; ORGANIC COMPOUND; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031013928     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02236-8     Document Type: Article

References (21)

1. (a) Torsell, K. G. B. Natural Product Chemistry, Wiley, Chichester, 1983;
2. (b) Manitto, P. Biosynthesis of Natural Products, Ellis Harwood,Chichester, 1981;
3. (c) Thomas, R. H. The Chemistry of Natural Products, Blackie and Sons, Glasgow, 1985;
4. (d) Cordell, G. A. Introduction to Alkaloids, A Biogenetic Approach, Wiley, New York, 1981.
5. For reviews see Sainsbury, M. Tetrahedron, 1980, 36, 3327; Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 9, 977.
6. For reviews see Sainsbury, M. Tetrahedron, 1980, 36, 3327; Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 9, 977.
7. Watanabe, T.; Miyaura, T.; Suzuki, A. Synlett, 1992, 207 and references therein; Stille, J. K. Angew. Chem., Int. Ed. Engl., 1986, 25, 508.
8. Watanabe, T.; Miyaura, T.; Suzuki, A. Synlett, 1992, 207 and references therein; Stille, J. K. Angew. Chem., Int. Ed. Engl., 1986, 25, 508.
9. Motherwell, W. B.; Pennell, A. M. K. J. Chem. Soc., Chem. Commun., 1991, 877.
10. (a) Benati, L.; Spagnolo, P.; Tundo, A.;. Zanardi, G. J. Chem. Soc., Chem. Commun. 1979, 141;
11. (b) Huppatz, J. L.; Sasse, W. H. F. Aust. J. Chem, 1963, 16, 417;
12. (c) Narsimhan, N. S.; Aidhen, I. S. Tetrahedron Lett., 1988, 29, 2987;
13. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
14. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
15. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
16. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
17. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
18. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
19. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
20. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.
21. (d) For particular cases involving sulfonyl substituted aromatic derivatives see, inter alia: Kohler, J. J.; Speckamp, W. N. Tetrahedron Lett., 1977, 18, 631; ibid 1977, 18, 635; Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567; Kohler, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1978, 166; ibid 1980, 142 and references therein; Clive, D. L. J.; Boivin, T. L. J. Org. Chem. 1989, 54, 1997; Feigenbaum, A.; Pete, J. P.; Scholler, D. J. Org. Chem., 1984, 49, 2355; Grimshaw, J.; Trocha, J. J. Chem. Soc., Perkin Trans. 1, 1979, 799. Bowman,W. R.; Heaney, H.; Jordan, B. M. Tetrahedron, 1991, 47, 10119.