The Rearrangement of Chromanone Oximes with Lithium Aluminum Hydride
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概要
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The lithium aluminum hydride reduction of 7-methoxychromanone oxime (I) and 7-methoxy-3-methylchromamone oxime (II) gave only the rearrangement product (the 2,3,4,5-tetrahydro-1,5-benzoxazepine derivative). 7-Methoxy-2-methylchromanone oxime (III) and 7-methoxy-2-isopropylchromanone oxime (IV) gave a mixture of the rearrangement product (secondary amine) and the normal reduction product (primary amine). 7-Methoxy-2-<I>t</I>-butylchromanone oxime (V) gave only the normal reduction product. The main conclusions to be drawn from these results are as follows: (1) The chromanone oximes without a C<SUB>2</SUB> substituent give only the rearrangement product. (2) The chromanone oximes with a C<SUB>2</SUB> substituent give a mixture of the normal reduction product and the rearrangement product. (3) The more bulky substituent at C<SUB>2</SUB> gives the more normal reduction product and the smaller quantity of the rearrangement product.
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