Stereoselective Bromination of 2-Vinyl Chromones Using NBS

REFERENCES

• (a) Bruneton , J. Pharmacognosy, Phytochemistry, and Medicinal Plants ; trans . C. K. Hatton ; Lavoisier Publishing : Paris , 1995 ; (b) Middleton Jr. , E. ; Kandaswami , C. The Flavonoids Advances in Research since 1986 , J. B. Harborne (Ed) ; Chapman and Hall : London , 1994 .
   Google Scholar
• Gammill , R. B. A new and efficient synthesis of 3–halogenated 4H-1-benzopyran-4-ones . Synthesis . 1979 , 901 – 903 .
   Google Scholar
• Silva , A. M. S. ; Pinto , D. C. G. A. ; Cavaleiro , J. A. S. ; Levai , A. ; Patonay , T. Synthesis and reactivity of styrlychromones . Arkivoc 2004 , 7 ; 106 – 123 .
   Web of Science ®Google Scholar
• Weiner , H. ; Sneen , R. A. Substitutions at saturated carbom atom, V: Clarification mechanism of solvolyses of 2-octyl sulfonates: Kinetic considerations . J. Am. Chem. Soc. 1965 , 87 ( 2 ), 292 – 296 .
   Web of Science ®Google Scholar
• Gupta , S. C. ; Yusuf , M. ; Sharma , S. ; Saini , A. ; Arora , S. ; Kamboj , R. C. Phototransformations of some 3-alkoxy-2-styrylchromones: Type II cyclisations of 1,4- and 1,6-biradicals . Tetrahedron 2004 , 60 , 8445 – 8454 .
   Web of Science ®Google Scholar
• (a) Silva , A. M. S. ; Vieira , J. S. ; Brito , C. M. ; Cavaleiro , J. A. S. ; Patonay , T. ; Levai , A. ; Elguero , J. Bromination and azidation reactions of 2-styrylcromones: New synthesis of 4(5)-aryl-5(4)-(2-chromonyl)-1,2,3-triazoles . J. Monatsh. Chem. 2004 , 135 , 293 – 308 ; (b) Saraf , B. D. ; Wadokar , K. N. Reactivity of 1,5-disubstituted-4-petene-1,3-diones: Part 1 Selective bromination of 1-(2-hydroxyphenyl)-5-phenyl-4-pentene-1,3-diones . Ind. J. Chem. 1988 , 27b , 771 – 772 .
   Web of Science ®Google Scholar
• Mikhailov , B. M. Nature of carbon–halogen bonds . Russ. Chem. Rev . 1971 , 983 – 995 .
   Google Scholar
• Mohamadi , F. ; Richards , N. G. J. ; Guida , W. C. ; Liskamp , R. ; Lipton , M. ; Caufield , C. ; Chang , G. ; Hendrickson , T. ; Still , W. C. MacroModel—An integrated software system for modeling organic and bioorganic molecules using molecular mechanics . J. Comput. Chem . 1990 , 11 , 440 – 467 .
   Web of Science ®Google Scholar
• Thaler , W. A. Methods in Free Radical Chemistry ; E. S. Huyser (Ed.) ; Marcel Dekker ; New York , 1970 ; 151 .
   Google Scholar
• (a) Lu , F. L. ; Naguib , Y. M. A. ; Kitadani , M. ; Chow , Y. L. An investigation of the photodecomposition of N-bromosuccinimide; The generation and reactivity of succinimidyl radical. Can. J. Chem. 1979, 57, 1967–1976; (b) Tanner , D. D. ; Darwish , D. ; Mosher , M. W. ; Bunce , N. J. Polar Radicals, III: A case against anchimeric assistance in the bromination of 1-bromobutane. J. Am. Chem. Soc . 1969, 91(26), 7398–7401.
   Web of Science ®Google Scholar
• Tanner , D. D. ; Rowe , J. E. ; Pace , T. ; Kosugi , Y. Polar radicals, VI: Bromination reaction with molecular bromine and n-bromosuccinimide: Apparent anomalies and similarities . J. Am. Chem. Soc. 1973 , 95 ( 14 ), 4705 – 4711 .
   Web of Science ®Google Scholar
• Sonnet , P. E. Olefin inversion . Tetrahedron 1980 , 36 , 557 – 604 .
   Web of Science ®Google Scholar