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Hydrocarbonylierende Cyclisierung von Dienen, 8. Cyclisierung von 1,4‐Dienen mit funktionellen Gruppen in 3‐Stellung
Author(s) -
Eilbracht Peter,
Hüttmann GerdErich,
Deußen Rainer
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230520
Subject(s) - chemistry , allylic rearrangement , functional group , stereochemistry , medicinal chemistry , reaction conditions , organic chemistry , catalysis , polymer
Hydrocarbonylating Cyclization of Dienes, 8 1 . – 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‐catalyzed 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 split 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.