ORGN 100 |
We have demonstrated the use of samarium metal in organic synthesis. In this paper, we describe the reaction of aldimines derived from multicyclic amines and samarium metal in the presence of iodine. We have observed that the product distribution from the reaction of imines with samarium depends on the steric crowding of the groups present at the nitrogen of the imines. With bulkier aromatic systems at nitrogen of the imines, the products are monoamines, instead of the usual diamines. This has been attributed to a simple Birch-type reduction of the double bond of the imines, as a result of the protonation of the ion radical by the solvent. The alternative path of a radical-radical coupling has proved difficult to occur due to a severe steric crowding. The intermediate amino compounds have been converted to a few derivatives that have anticancer activity.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |