Publication details

T-Shaped Molecular Building Blocks by Combined Bridgehead and Bridge Substitution on Bicyclo[1.1.1]pentanes

Authors

KALETA Jiří MICHL Josef MAZAL Ctibor

Year of publication 2010
Type Article in Periodical
Magazine / Source Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Web http://pubs.acs.org/doi/abs/10.1021/jo100169b
Field Organic chemistry
Keywords organic synthesis;bicyclopentanes;strained compounds;molecular building blocks
Description Derivatives of bicyclo[1.1.1]pentane differentially substituted in bridgehead (1,3) and bridge (2,4) positions have been synthesized. They represent a new T-shaped structural module consisting of a rigid rod with a nearly freely rotating side arm, possibly useful as a molecular building block in syntheses of more complex covalent or supramolecular scaffolds useful in bottom-up construction of molecular level devices or materials. For good chemical connectivity in the axial direction, carboxylates, ethynyls, and acetylsulfanyl groups were installed at the bridgeheads. Quinoxalines were attached in the transverse direction through a highly reactive alpha-diketone system located at the bridges.
Related projects: