This proposal outlines plans to utilize transition metal organometallic reagents to develop new synthetic methods for forming carbon-carbon (C-C) and carbon-nitrogen (C-N) bonds in organic molecules. In the C-C area, the research concentrates on reactions which involve insertion of acetylenes into metal-carbon bonds, and thus is directed toward the synthesis of substituted alkenes. Particular attention will be paid to the intramolecular version of this reaction, which can be applied to the construction of five-membered rings, such as those found in prostaglandins and the D-ring of steroids. In the C-N area, the proposal focuses on insertion of NO into metal-carbon bonds. This provides a way of incorporating nitrogen atoms into organic molecules using NO gas as a source of nitrogen. Two types of reaction will be investigated. In the first, another reactive functionality X in a molecule R-X is replaced by a nitrogen atom. The second type involves 1,2-diamination (and 1,2 addition of a nitrogen function and CO fragment) to an alkene. This reaction generates functionality found in a wide range of physiologically active, nitrogen-containing organic molecules, such as alkaloids, amino acids, analgesics, and antihypertensive agents.
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