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PubMed · 16411735

The chain-length dependence test.

Matthew T Stone·Jennifer M Heemstra·Jeffrey S Moore
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Abstract

Trends obtained from systematic studies based on chain-length variation have provided valuable insight and understanding into the behavior of m-phenylene ethynylene foldamers. The generalization of this experimental approach, the chain-length dependence test, is useful for studying solution conformation, packing in the solid state, specific intrachain interactions, and the contributions of end groups to a particular property.

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Macrocyclic CompoundsModels, MolecularMolecular ConformationMolecular StructurePolymersStructure-Activity RelationshipThermodynamicsJournal ArticleResearch Support, U.S. Gov't, Non-P.H.S.Review

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Matthew T Stone, Jennifer M Heemstra, Jeffrey S Moore. 2006. The chain-length dependence test.. https://doi.org/10.1021/ar0501267

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Polyether macrocycles from intramolecular cyclopropanation and ylide formation. Effect of catalyst and coordination.

The use of catalytic metal carbene methodology with diazoacetates for the construction in high yield of polyether macrocycles having ring sizes greater than 25 has been achieved by preventing access to gamma-C-H positions for intramolecular insertion. Cyclopropanation is the exclusive outcome of reactions performed with dirhodium(II) catalysts, and product yields of greater than 70% are obtained without resorting to high dilution with solvents. With copper(I) catalysts having multiple sites for polyether coordination, intramolecular oxonium ylide formation occurs at the terminal oxygen, followed by [2,3]-sigmatropic rearrangement of the pendant allyl group, in competition with cyclopropanation. Sodium ion coordination with the reactant diazo compound inhibits oxonium ylide formation in copper-catalyzed reactions. The composite results are consistent with copper serving as a template for the substrate as well as the site in the ether complex for diazo decomposition and subsequent metal carbene reactions.

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