Liquid chromatographic isolation and structural elucidation of methoxymethylene dimethyl dodecatrienes catalytically synthesized from methanol and three moles of isoprene

Add time:09/04/2019    Source:sciencedirect.com

The palladium-catalysed reaction of isoprene with methanol yields methoxy dimethyl octadienes (“methoxy dimers”) and dimers of isoprene. To obtain additional information about the mechanism of catalysis this paper is aimed at identifying the higher boiling side-products of this reaction. After distillation in high vacuum the residue of the reaction was separated by analytical and preparative reversed-phase and normal-phase high-performance liquid chromatography, yielding at least six compounds with the formula C16H28O (“methoxy trimers”) plus trimers and tetramers of isoprene, all proven by mass spectra. The structure of two methoxy trimers was elucidated by 1H and 13C NMR spectra. Up until now they have not been described in the literature and they show an unexpected position of the methoxy group.

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