Reaction of Lithium Aluminum Hydride with Hindered Phenols. Formation of Tricoordinate Aluminum Species

Article abstract of DOI:10.1021/jo01305a014

Lithium aluminum hydride reacts readily with 3 molar equiv of 2,4,6-tri-tert-butylphenol in refluxing ether.It has been demonstrated that the products resulting from this reaction cause the conversion of axial to equatorial cyclohexanols in the presence of a ketone.This behaviour is attributed to the formation of tricoordinate aluminum species.An ether solution of bis(2,4,6-tri-tert-butylphenoxy)aluminum hydride was prepared, and infrared spectra provide evidence for the existence of this species in solution resulting from the reaction of LiAlH4 with 3 molar equiv of 2,4,6-tri-tert-butylphenol.