Remarkable Solvent Control of Functional Group Selectivity in Complex Metal Hydride Reductions

Article abstract of DOI:10.1021/jo01300a071

Lithium aluminium hydride in ethyl ether reduces alkyl tosylates to the corresponding alkanes rapidly and selectively in the presence of alkyl iodides and bromides without concurrent attack on halogen, whereas in diglyme the reactivity order is reversed, alkyl iodides and bromides being reduced selectively without significant attack on alkyl tosylates.