Reductions with lithium aluminum hydride have been characterized by the high degree of predictability of the products (1). In a few instances groups were anomalously reduced due to the structure of the compound treated with this reagent (1). Recently, however, three interesting molecular rearrangements have been reported to occur with lithium aluminum hydride indicating a new type of reaction with this reagent. Cram (2) has shown that the phenyl groups of the ptoluenesulfonic acid esters of either 2-phenyl-3-pentanol or 3-phenyl-2-pentanol undergo rearrangement by a Wagner-Meerwein reaction to form a mixture of 2and 3-phenylpentane on treatment with lithium aluminum hydride. Cope (3) reported the formation of bicyclo[3.3.0]octane-l-methanol by a reductive rearrangement, resembling a Favorski rearrangement, of bicyclo[3.3.1]nonan-9one. N-Ethyl-and N-propyl-aniline have been isolated in addition to the ex-SUMMARY Acetophenone oxime and six para-substituted-acetophenone oximes were reduced with lithium aluminum hydride. The products from normal reduction, 1 -(p-substituted-phenyl) -1-ethylamine (I), and from reduction with rearrangement, p-substituted-N-ethylaniline (II), were isolated from every reaction. The yield of the product of reductive-rearrangement, II, was shown to increase with an increase in electron-releasing capacity of the para-substituent.