- Hydrocarbonylating Cyclization of Dienes, 8. - Cyclization of 1,4-Dienes with Functional Groups in 3-Position
-
1,4-Dienes 1a-i with functional groups at C-3 were synthesized and treated under the conditions of metal-cytalyzed hydrocarbonylating cyclization.Under the usual conditions no cyclization products could be isolated.Modifications of the reaction conditions did not lead to the expected cyclopentanones of type 2 or 3 either.Instead, the original functional groups are slit off.Depending on the reaction conditions, either the non-functionalized 2-cyclopentenones 5, the cyclopentanones 6, or the 2-cyclopentenones 7 with a functional group introduced from the solvent into the 2-methyl group are obtained.These unexpected products of type 7 at least formally correspond to allylic rearrangement products of the expected but not observed type-3 exo-methylenecyclopentanones.The mechanism of the formation of these products is discussed.
- Eilbracht, Peter,Huettmann, Gerd-Erich,Deussen, Rainer
-
p. 1063 - 1070
(2007/10/02)
-