Synthesis p. 1053 - 1056 (1990)
Update date:2022-08-04
Topics:
Nidy
Graber
Spinelli
Sih
Johnson
A synthetic route to tercyclohexanones is described in which alkylation of 4-cyclohexylcyclohexanone with the dianion of 4,4-(ethylenedioxy)cyclohexanecarboxylic acid gives 1-carboxy-1'-hydroxyl-1,1':4',1''-tercyclohexan-4-one ethylene ketal. Decarboxylative dehydration of the latter followed by hydrolysis of the ketal gives 4-(4'-cyclohexylcyclohexylidene)cyclohexanone. Hydrogenation of this compound gives cis- and trans-1,1':4',1''-tecyclohexan-4-one, the latter of which is correlated with authentic trans-1,1':4',1''-tercyclohexane.
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Doi:10.1016/j.bmcl.2011.01.051
(2011)Doi:10.1039/DT9900003465
(1990)Doi:10.1021/jm00108a019
(1991)Doi:10.1016/j.bmcl.2018.01.043
(2018)Doi:10.1002/jhet.1769
(2014)Doi:10.1021/jm00108a007
(1991)