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Issue 10, 2014
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Selective isomerization–carbonylation of a terpene trisubstituted double bond

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Abstract

Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)2] as a catalyst precursor occurs with >97% selectivity for the terminal diester dimethyl-3,7-dimethylnonane-dioate. This prevails much over the typical cationic methoxyaddition. The reactive primary carboxy group formed allows for e.g. the preparation of the high molecular weight novel polyester poly[3,7-dimethylnonanediyl-3,7-dimethylnonanedioate].

Graphical abstract: Selective isomerization–carbonylation of a terpene trisubstituted double bond

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Publication details

The article was received on 02 Jul 2014, accepted on 18 Aug 2014 and first published on 03 Sep 2014


Article type: Communication
DOI: 10.1039/C4GC01233J
Citation: Green Chem., 2014,16, 4541-4545

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    Selective isomerization–carbonylation of a terpene trisubstituted double bond

    H. Busch, F. Stempfle, S. Heß, E. Grau and S. Mecking, Green Chem., 2014, 16, 4541
    DOI: 10.1039/C4GC01233J

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