Reaction of Thexylalkoxyboranes with Selected Orgnic Compounds Containing Representative Functional Groups Comparison of Reducing Characteristics of the Alkoxy Derivatives

The reaction of alcohol with a solution of thexylborane (ThxBH2) in tetrahydrofuran (THF) provides a new class of mild and selective reducing agents, thexylalkoxyboranes (ThxBHOR: R=Et, i-Pr, i-Bu, s-Bu, t-Bu, Ph). In order to elucidate the effect of the alkoxy group in reduction reactions, the reducing power of ThxBHOR toward selected organic compounds containing representative functional groups under practical conditions (THF, 25°, the quantitative amount of reagent to compound) has been investigated. Generally, the reactivity of ThxBHOR is largely dependent upon the alkoxy substituent. ThxBHOR can be synthesized from a variety of alcohols, thus allowing control of the steric and electronic environment of these reagents.