Anomalous lithium aluminum hydride reduction of carbon—carbon double bonds in 7-azabicyclo(2.2.1)heptenyl systems
✍ Scribed by Alan P. Marchand; Robert W. Allen
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 164 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Recent interest in the mechani.sm of lithium aluminum hydride (LAH) reductions of formally isol-6 lated carbon-carbon double bonds proqts us to report our observations for the corresponding reductions in szabicyclic systems.
📜 SIMILAR VOLUMES
Indium hydride (Cl 2 InH) generated in situ from a combination of a catalytic amount of indium(III) chloride and sodium borohydride selectively reduces the carbon carbon double bond in conjugated alkenes such as a,a-dicyano olefins, a,b-unsaturated nitriles, cyano esters, cyanophosphonate, diesters
Neighboring group participation of oxygen in the mechanism of lithium aluminum hydride (LAH) reductions of carbon-carbon multiple bonds is well documented. 2-8 On the other hand,
Absmcf: 1,2-Dihalocyclop%enes on reaction with alkali metals and chlomlrimethylsilane in hydmcarbon or ether solvents produce silylatcd I-pentynes by ring opening. Sodium metal and hydrwarbon solvents favour the cleavage most. Different mechanistic aspxts are considered.