Premium
Hydrocarbonylierende Cyclisierung von Dienen, 7. Cyclisierung von 1,4‐Dienen mit funktionalisierten Seitenketten an C‐3
Author(s) -
Eilbracht Peter,
Hüttmann GerdErich
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.19901230519
Subject(s) - chemistry , aldehyde , rhodium , medicinal chemistry , alkoxy group , side chain , catalysis , carboxylic acid , organic chemistry , stereochemistry , alkyl , polymer
Hydrocarbonylating Cyclization of Dienes, 7 1 . – Cyclization of 1,4‐Dienes Containing Functionalyzed Side Chains at C‐3 In 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.