Specific synthesis of 1,2- and 1,3-dialkylidenecycloheptanes by [3+2+2] cyclization of alkenyl Fischer carbene complexes and allenes.

doi:10.1021/JA045459Y

Paper

Specific synthesis of 1,2- and 1,3-dialkylidenecycloheptanes by [3+2+2] cyclization of alkenyl Fischer carbene complexes and allenes.

Published Oct 13, 2004 · J. Barluenga, R. Vicente, Pablo Barrio

Journal of the American Chemical Society

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Abstract

The 1,2- and 1,3-dialkylidenecycloheptane rings are specifically assembled from chromium alkenyl Fischer carbene complexes and allenes via [3+2+2] cyclization reactions. The former cycloadducts are obtained when the cyclization is performed in the presence of 1 equiv of [Ni(cod)2], while the [Rh(cod)Cl]2-catalyzed cyclization leads to the latter cycloadducts.

Study Snapshot

This study presents a specific synthesis of 1,2- and 1,3-dialkylidenecycloheptanes from chromium alkenyl Fischer carbene complexes and allenes, with potential applications in organic synthesis and catalysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Specific synthesis of 1,2- and 1,3-dialkylidenecycloheptanes by [3+2+2] cyclization of alkenyl Fischer carbene complexes and allenes.

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References

Citations

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Recent advances in catalytic assembly of cyclopentene cores using various synthetic methodologies, including transition metal-catalyzed and organocatalyzed processes, have significantly improved our understanding of this structural motif.

Reactions of Rhenacyclobutadiene Complexes with Allenes

Rhenacyclobutadiene complexes can selectively react with electron-rich aminoallenes, producing methylenecyclopentene and 1,3-dimethylenecyclopentane derivatives depending on the steric properties of OR groups and aminoallenes.

Fischer Carbene Complexes: A Glance at Two Decades of Research on Higher-order Cycloaddition Reactions.

Fischer carbene complexes (FCCs) can generate highly selective compounds with a broad range of scaffolds, offering potential for organic synthesis.

Diastereoselective Rhodium‐Catalyzed [(3+2+2)] Carbocyclization Reactions with Tethered Alkynylidenecyclopropanes: Synthesis of the Tremulane Sesquiterpene Natural Products

Rhodium-catalyzed [(3+2+2)] carbocyclization reactions enable efficient syntheses of tremulane sesquiterpene natural products, with high levels of stereocontrol achieved.

Transition-Metal-Catalyzed Cycloaddition Reactions to Access Seven-Membered Rings.

Transition-metal-catalyzed cycloaddition reactions enable efficient and selective synthesis of functionalized seven-membered rings, with potential for diverse synthetic strategies.