ISSN:
0009-2940
Keywords:
Carbonylation of 1,4-dienes
;
Cyclopentanone synthesis
;
Catalysis, functional groups in
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Hydrocarbonylating Cyclization of Dienes, 71. - Cyclization of 1,4-Dienes Containing Functionalyzed Side Chains at C-3In order to test, whether functional groups are tolerable in rhodium- or cobalt-catalyzed hydrocarbonylating cyclizations of 1,4-dienes 1 to substituted cyclopentanones 2, various dienes of type 3 with functionalyzed side chains in C-3 were synthesized and treated under cyclization conditions. Ester, hydroxy, alkoxy, and acetate groups proved to be sufficiently stable (the latter only in rhodium-catalyzed conversions), so that the corresponding cyclopentanones 4 could be obtained in medium to good yields. Free carboxylic acid and aldehyde groups, however, prevented the formation of significant amounts of cyclization products. Pentenynes of type 6 under analogous conditions yielded at best only minor amounts of cyclopentanones.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230519
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