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Ruthenium‐Catalyzed Cross Metathesis of β‐Myrcene and its Derivatives with Methyl Acrylate
Author(s) -
Behr Arno,
Johnen Leif,
Wintzer Andreas,
Gümüş Çetin Arzu,
Neubert Peter,
Domke Lutz
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500993
Subject(s) - myrcene , ruthenium , methyl acrylate , metathesis , ring closing metathesis , chemistry , catalysis , acrylate , organic chemistry , yield (engineering) , salt metathesis reaction , polymer chemistry , medicinal chemistry , materials science , polymerization , copolymer , polymer , chromatography , essential oil , limonene , metallurgy
The reaction of β‐myrcene with methyl acrylate produces 3‐methylenecyclopent‐1‐ene in the presence of the Ru catalyst Neolyst M2 by ring‐closing metathesis in the first step. In the second step, the generated methylidene unit reacts with methyl acrylate to give the corresponding unsaturated cyclic ester by cross metathesis. Under the optimized reaction conditions (80 °C, Neolyst M2, 16 equivalents of methyl acrylate), derivatives of β‐myrcene, myrcenol, myrcenyl acetate, and β‐ocimene, react to yield functionalized acyclic esters.