REACTION OF ALUMINUM-HYDRIDE TRIETHYLAMINE COMPLEX WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS

The addition of triethylamine to a solution of aluminum hydride in tetrahydrofuran (THF), which was prepared by the addition of a calculated amount of hydrogen chloride in diethyl ether to solutions of sodium aluminum hydride in THF, provides very stable solutions of aluminum hydride-triethylamine complex (AHTEA). The reducing power of AHTEA complex in tetrahydrofuran toward 59 selected organic compounds containing representative functional groups under practical conditions (tetrahydrofuran, room temperature, the quantitative amount of reagent to compound) has been investigated. In this way, we have established that quantitative reduction of various organic functionalities can be readily achieved using the calculated quantity of AHTEA to avoid the use of excess reagent. This permits ready use of the aluminum hydride reagent in organic synthesis with high convenience and efficiency, with the possibility of an improved selectivity than that of aluminum hydride itself in tetrahydrofuran.