α-Allylation of Aryl- or Heteroarylketones via the Claisen Rearrangement

References

• Yoshioka , H , Takesaki , K. , Kobayashi , M. and Matsumoto , T. 1979 . Tetrahedron Lett. , : 3489
   Google Scholar
• Martin , S. F. and Chou , T.-S. 1978 . Tetrahedron Lett. , : 1943
   Google Scholar
• Negeshi , E. and Luo , F.-T. 1983 . J. Org. Chem , 48 : 2427
   Google Scholar
• Tsuji , J. 1980 . J. Organic Synthesis with Palladium Compounds , 125 Heidelburg : Springer Verlag .
   Google Scholar
• Lansbury , P. T. , Nienhouse , E. J. , Scharf , D. J. and Hilfiker , F. R. 1970 . J. Amer. Chem. Soc. , 92 : 5649
   Google Scholar
• Trost , B. M. 1980 . Accts. Chem. Res. , 13 : 385
   Web of Science ®Google Scholar
• Rhoads , S. J. and Paulins , N. R. 1975 . Org. Reactions , 22 : 1
   Web of Science ®Google Scholar
• Tsuji , J. , Shimizu and Kobayashi Isr , Y. 1984 . J. Chem. Soc. , 24 : 153
   Google Scholar
• Ponaras , A. A. 1983 . J. Org. Chem. , 48 : 3866
   Web of Science ®Google Scholar
• Denmark , S. E. and Harmata , M. A. 1982 . J Amer. Chem. Soc. , 104 : 4972
   Google Scholar
• Inoue , Y. , Toyofuk , M. , Taguchi , M. , Okada , S. and Hashimoto , H. 1986 . Bull. Chem. Soc. Jpn. , 59 : 885
   Google Scholar
• Schuda , P. F. and Bernstein , B. 1984 . Syn. Comm. , 14 : 293
   Web of Science ®Google Scholar
• Ziegler , F. E. 1988 . Chem. Rev. , 88 : 1423 and references therein
   Web of Science ®Google Scholar
• Brannock , K. C. 1959 . J. Am. Chem. Soc. , 81 : 3379
   Web of Science ®Google Scholar
• Lorette , N. B. and Howard , W. L. 1961 . J. Org. Chem , 26 : 3112
   Web of Science ®Google Scholar
• Dolby , L. J. , Elliger , C. A. , Esfandiary , S. and Marshall , K. S. 1968 . J. Org. Chem. , 33 : 4508
   Google Scholar
• Daub , G. W. and Lunt , S. R. 1983 . Tetrahedron Lett. , 24 : 4397
   Google Scholar
• Attempts to alkylate the enolates of pyridocycloalkanones as shown in Table by allyl bromide, ethyl bromoacetate, and other electrophiles failed. In the presence of even weak bases such as pyrrolidine the azaindanone 1 produced a dark blue mixture in which only the unchanged ketone could be recognized
   Google Scholar
• Thummel , R. P. , Lefoulon , F. , Cantu , D. and Mahadevan , R. J. 1984 . J. Org. Chem. , 49 : 2208
   Web of Science ®Google Scholar
• Sugimoto , N. , Kugita , H. and Tanaka , T. 1956 . J. Pharma. Soc. Japan , 76 : 1308
   Google Scholar
• Jones , D. G and Jones , G. 1969 . J. Chem. Soc. (C) , : 707
   Google Scholar
• The ketone was synthesized according to the procedure of Sugimoto et al. 9a
   Google Scholar
• The vinyl allyl ether intermediate appeared to show up in the tlc plate as a bright fluorescent UV-active spot during the reaction. The fluorescent UV-active spot was characteristic for this intermediate in the reaction, as the α-allyl ketone was formed at the expense of the spot
   Google Scholar
• β-tetralone was also tried. As expected the reaction failed due to instability or aromatization of the molecule
   Google Scholar
• Satisfactory spectral data (NMR and IR) were obtained for all new compounds along with satisfactory elemental analyses where physical constants are indicated
   Google Scholar
• Bravo , P. , Piovosi , E. , Resnati , G. and Fronza , G. 1989 . J. Org. Chem. , 54 : 5171
   Web of Science ®Google Scholar
• Huh , T.-S. , Neumeister , J. and Griesbaum , K. 1981 . Can. J. Chem. , 59 : 3188
   Google Scholar
• Detailed information is forthcomming
   Google Scholar
• Hatch , L. F. , Alexander , H. E. and Randolph , J. D. 1950 . J. Org. Chem. , 15 : 654
   Google Scholar
• The elemental analysis: Calc'd for C12H11 BrNO. HC1: C, 47. 63; H, 4. 33; Br, 26.41; Cl, 11.72; N, 4.63. Found: C, 47.90; H, 4.29; Br, 26.45; Cl, 11.74; N, 4.58
   Google Scholar