Complexing of terpenes with transition metals. Part V. Reactions of 3,7-dimethylocta-1,6-diene and of 7-methoxy-3,7-dimethyloct-1-ene with rhodium(III) and thallium(III)
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 20,p. 2092-2096
- https://doi.org/10.1039/p19750002092
Abstract
3,7-Dimethylocta-1,6-diene and 7-methoxy-3,7-dimethyloct-1-ene are catalytically oxidised at the vinyl group by RhCl3–FeCl3 in oxygen to the derived methyl ketones in good yield. An accompanying alkene isomerisation reaction (–CMe·CH:CH2→–CMe:CH·CH3) has been studied. The above octadiene and methoxyoctene are hydroformylated (–CMe·CH:CH2→–CMe·CH2·CH2·CHO) in good yield by [RhH(CO)(PPh3)3], with some accompanying alkene isomerisation. With Tl(NO3)3, 3,7-dimethylocta-1,6-diene reacts at the 6,7-double bond to give a ketone with migration of a methyl group, and at the 1,2-double bond with cyclisation to give cyclopentane derivatives.Keywords
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