Bulletin of the Academy of Sciences of the USSR Division of Chemical Science p. 517 - 521 (1990)
Update date:2022-08-29
Topics:
Moiseenkov, A. M.
Cheskis, B. A.
Shpiro, N. A.
Stashina, G. A.
Zhulin, V. M.
The dimerization of methyl acrylate to dimethyl α-methyleneglutarate by the action of tributylphosphine in the absence of a solvent was investigated.Methyl α-methylene-β-hydroxypentanoate was obtained with a moderate yield by the condensation of propionaldehyde with methyl acrylate catalyzed by triphenylphosphine or 1,4-diazabicyclo<2.2.2>octane and initiated by high pressure.In the last of these data a three-stage stereospecific synthesis of dominicalures 1 and 2 (components of the aggregation pheromone of the grain beetle) was realized from sec-amyl acrylate and propionaldehyde or isobutyraldehyde.
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