A new type of allylation: synthesis of β,γ-unsaturated ketones from α-halogenated aryl ketones using an allyltributyltin(IV)–tin(II) dichloride–acetonitrile system
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Makoto Yasuda, Makihiro Tsuchida and Akio Baba
Abstract
Allylation of α-halogenated aryl ketones with an allyltributyltin–tin dichloride–acetonitrile system gave β,γ-unsaturated ketones in high yields via selective aryl rearrangement.
References
A recent review: Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207 Search PubMed.
M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata and A. Baba, Tetrahedron Lett., 1996, 37, 5951 CrossRefCAS.
α-Halogenated ketones are an important class of organic compound and information on their synthesis has been reported.
N. De Kimpe and
R. Verhé,
The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, ed.
S. Patai and Z. Rappoport,
Wiley,
Chichester,
1988 Search PubMed.
Y. Naruta, S. Ushida and K. Maruyama, Chem. Lett., 1979, 919 CAS.
We have recently reported a similar rearrangement of a 2-oxoalkyl group promoted by
ZnCl2. In this case, however, there was no observation of the aryl rearrangement even with the use of an aromatic substrate. M. Yasuda, S. Tsuji, I. Shibata and A. Baba, J. Org. Chem., 1997, 62, 8282 Search PubMed.
I. Pri-Bar, P. S. Pearlman and J. K. Stille, J. Org. Chem., 1983, 48, 4629 CrossRefCAS.
K. Yano, Y. Hatta, A. Baba and H. Matsuda, Synlett, 1991, 555 CrossRefCAS.
K. Yano, Y. Hatta, A. Baba and H. Matsuda, Synthesis, 1992, 7, 693 CrossRef.
The migratory aptitude for pinacol rearrangement of various aromatic substituents has been reported. W. E. Bachmann and J. W. Ferguson, J. Am. Chem. Soc., 1934, 56, 2081 Search PubMed.
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