[en] The light-induced isomerisation of allylic ethers in the presence of pentacarbonyliron has been compared with that brought about by a basic heterogeneous catalyst, KNH2-Al2O3. The reaction on the basic catalyst proceeds through the usual cis-mechanism. In contrast, the carbonyliron reaction gives cis- and trans-isomers, in a 1:1 ratio in the case of allyl phenyl ether. A π-complex was detected (by n.m.r. spectroscopy) as an intermediate in the reaction. The formation of a catalyst which was particularly active for the thermal isomerisation of olefinic double bonds was detected during the irradiation of pentacarbonyliron in allyl phenyl ether. 3-Propoxycyclohexene was readily isomerised under these conditions, whereas it remained unchanged in the presence of very strong bases. Conformational effects of the ring were observed.
Disciplines :
Chemistry
Author, co-author :
Hubert, André J.
Georis, A.; Université de Liège - ULiège
Warin, R.; Université de Liège - ULiège
Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Base-catalysed prototropic rearrangement. Part I. Comparison of the base-catalysed and the metal carbonyl-catalysed isomerisation of allyl ethers
Publication date :
1972
Journal title :
Journal of the Chemical Society, Perkin Transactions 2
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