- Rationalisation of patterns of competing reactivity by x-ray structure determination: Reaction of isomeric (benzyloxythienyl)oxazolines with a base
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Three isomeric (benzyloxythienyl)oxazolines 9, 11 and 13 have been prepared and are found, upon treatment with a strong base, to undergo either Wittig rearrangement or intramolecular attack of the benzylic anion on the oxazoline function to give products derived from cleavage of the initially formed 3-aminothienofuran products. This pattern of reactivity is directly linked to the distance between the two reactive groups as determined by X-ray diffraction, with the greatest distance in 11 leading to exclusive Wittig rearrangement, the shortest distance in 13 giving exclusively cyclisation-derived products, and the intermediate distance in 9 leading to both processes being observed. The corresponding N-butyl amides were also obtained in two cases and one of these undergoes efficient Wittig rearrangement leading to a thieno[2,3-c]pyrrolone product.
- Aitken, R. Alan,Harper, Andrew D.,Slawin, Alexandra M. Z.
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- 4,6-Diphenylthienofuran
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The oxazolinium iodide 9 reacts with phenylmagnesium bromide to give 4,6-diphenylthienofuran (5b).Some reactions, the X-ray structure analysis, luminescence spectra, and theoretical investigations are described. - Keywords: Thienofuran; Luminescence spectra; AM1 calculations
- Schoening, Axel,Debaerdemaeker, Tony,Zander, Maximilian,Friedrichsen, Willy
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p. 1119 - 1132
(2007/10/02)
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