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W. Abel, F. G. A. Stone, G. Wilkinson). Pergamon, Oxford, 1995, Vol. 1, 1. 23. ; Snieckus, V. In: Comprehensive organometallic chemistry II (ed. E. W. Abel, F. G. A. Stone, G. Wilkinson). Pergamon, Oxford, 1995, Vol. 11, 1. 24. Wakefield, B. J. Organolithium Method. Academic Press, London, 1988. 25. ; Maruoka, K. Angew. Chem. Int. Ed Engl, 1997,36,1183. 26. ; Yamamoto, H. J. Am. Chem. Soc. 1992,114,1089. 27. ; Yamamoto, H. Bull. Chem. Soc. Jpn 1988, 61, 2975. 28. ; Yamamoto, H. J. Am. Chem. Soc.
15. Filter the contents of the flask with the aid of three 50 mL portions of dichloromethane. The sodium fluoride-water workup offers an excellent method for large-scale preparations, and is generally applicable for product isolation in the reaction of organoaluminium compounds. 16. Evaporate the combined filtrates under reduced pressure with a rotary evaporator. 17 g (94-95%) of diphenylacetaldehyde as a colourless oil, which is characterized by 'H NMR analysis. Although the acid-catalysed rearrangement of epoxides to carbonyl compounds is a well-known transformation and a number of reagents have been elaborated for this purpose, only a few reagents have been used successfully for the rearrangement of functionalized epoxides with respect to the efficiency and selectivity of the reaction.
The catalytic activities of diarylborinic acids 2 and 3 are much higher than those of the corresponding arylboronic acids. * The dehydration is strongly promoted in tetrahydrofuran (THF). 6 a,p-enones are obtained as E isomers in high yields. In the reaction of a-substituted-(3-hydroxy carbonyl compounds, a,(3-enones are preferentially obtained from anti-a\do\s, and most of the 5yn-aldols are recovered. Thus, the present dehydration is a useful and convenient method for isolating pure synaldol from syn- and a«r/-isomeric mixtures.