Activation of C-H bonds in saturated hydrocarbons. The formation of bis(triphenylphospine)(η-alkadiene)rhenium trihydrides from n-Alkanes, and their selective conversion into the corresponding 1-alkenes
✍ Scribed by Denise Baudry; Michel Ephritikhine; Hugh Felkin; Janusz Zakrzewski
- Book ID
- 104232582
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 260 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
n-Alkanes (C,-C,) react at 7O'C with bis(triphenylphosphine)rhenium heptahydride and 3,3-dimethylbutene to afford equilibrium mixtures of the corresponding bis(triphenylphosphine)(n-conjugated-diene)rhenium trihydrides; treatment of these mixtures with trimethylphosphite at 60°C converts them, in >95% yield and with >98% selectivity, into the corresponding 1-alkenes.
The chemistry of n-alkanes is limited, and the few reactions they undergo (with radical reagents and electrophiles) are generally rather unselective.
n-Pentane has, however, recently been converted into the (n-pentadiene)rhenium trihydride z, and the reaction of this with trimethylphosphite affords l-pentene in 95% yield (Scheme l).' Here we report the functionalisation of the higher n-alkane homologues 4a-c.