14 Indeed, the less nucleophilic benzene (N < −4.47) did not trap the 4-
methoxyphenyl cation in MeCN or AcOEt, while with 2,3-dimethyl-
2-butene (N = −1.0) arylation occurred efficiently (ca. 70% yield),see
ref. 6a.
15 For a recent reviews on allylsilane chemistry, see: L. Chabaud,
P. James and Y. Landais, Eur. J. Org. Chem., 2004, 3173.
16 K. Omura and T. Matsuura, Synthesis, 1971, 28.
17 D. Mangion and D. R. Arnold, Can. J. Chem., 1999, 77, 1655.
18 Examples of this radicalic fragmentation have been reported, see:
M. A. Miranda and F. Galindo, Photo-Fries reaction and related
processes, in CRC Handbook of Organic Photochemistry and Photo-
biology, ed. W. Horspool and F. Lenci, CRC Press, Boca Raton, 2nd
edn., 2004, p. 42-1.
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O r g . B i o m o l . C h e m . , 2 0 0 5 , 3 , 2 8 6 8 – 2 8 7 1
2 8 7 1