121950-69-4Relevant academic research and scientific papers
Reaction of α,β-Unsaturated Acid Chlorides with 4,4-Disubstituted Cyclohexanone Enamines
Ahmed, M. Giasuddin,Huque, A. K. M. Fazlul,Ahmed, S. Asghari,Mosihuzzaman, Mohammed,Andersson, Rolf
, p. 2815 - 2835 (2007/10/02)
Acrylyl and crotonyl chlorides react with the morpholine enamine of ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate to give ethyl 2-hydroxy-4,6-dioxo-2-methyladamantane-1-carboxylate and ethyl 2-hydroxy-4,6-dioxo-2,10-dimethyladamantane-1-carboxylate respectively.Reaction between crotonyl chloride and morpholine enamine of 4-acetyl-4-methylcyclohexanone proceeds in a similar manner and produces 6-hydroxy-6,7,9-trimethyladamantane-2,4-dione.The corresponding reaction with acrylyl chloride gives a mixture of 6-hydroxy-6,7-dimethyladamantane-2,4-dione and 1-methyl-4-morpholinotricyclo4,9>undecane-2,6-dione, of which the latter was isolated in pure form.The structure of the compounds have been determined by 1H and 13C n. m. r. and mass spectrometry.The course of reactions leading to the formation of different products as well as the stereochemistry of the chiral centres at C-6 and C-9 (or C-2 and C-10) of the adamantane derivatives have been discussed.
