A5048070665- Synthesis and Properties of Aromatic Compounds
- Organic Electronics and Photovoltaics
- Microbial Natural Products and Biosynthesis
- Molecular Junctions and Nanostructures
- Alkaloids: synthesis and pharmacology
- Advanced Synthetic Organic Chemistry
- Organic Chemistry Cycloaddition Reactions
- Chemical Synthesis and Analysis
- Crystallization and Solubility Studies
- Oxidative Organic Chemistry Reactions
- Supramolecular Chemistry and Complexes
- Catalytic C–H Functionalization Methods
- X-ray Diffraction in Crystallography
- Advanced Chemical Physics Studies
California Polytechnic State University
2017-2019
University of California, Los Angeles
2019
Abstract Reported herein is a one‐pot protocol for the oxodealkenylative introduction of carbonyl functionalities into terpenes and terpene‐derived compounds. This transformation proceeds by Criegee ozonolysis an alkene, reductive cleavage resulting α‐alkoxy hydroperoxide, trapping generated alkyl radical with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO), subsequent oxidative fragmentation MMPP. Using readily available starting materials from chiral pool, variety carbonyl‐containing products...
An <italic>ortho</italic>-naphtho diradical! Quinoidal forms in <italic>para</italic>- and <italic>meta</italic>-patterns lie at the extremes for closed-shell diradical fluorenofluorenes, respectively. <italic>ortho</italic>-Conjugation gives an intermediate case with partial character.
The [2,1-a]- and [1,2-a]-isomers of fluorenofluorenedione have been synthesized via intramolecular Friedel–Crafts acylations. DFT calculations indicate that the [1,2-a]-isomer adopts a twisted, helical C2-symmetric structure its protonated form is thermodynamic product acylation in hot sulfuric acid. Absorption spectroscopy cyclic voltammetry measurements provide experimental estimations frontier molecular orbital energy levels, which are reported discussed.
Abstract Reported herein is a one‐pot protocol for the oxodealkenylative introduction of carbonyl functionalities into terpenes and terpene‐derived compounds. This transformation proceeds by Criegee ozonolysis an alkene, reductive cleavage resulting α‐alkoxy hydroperoxide, trapping generated alkyl radical with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO), subsequent oxidative fragmentation MMPP. Using readily available starting materials from chiral pool, variety carbonyl‐containing products...
A strained, cyclic hydrocarbon comprising a meta ‐quaterphenyl‐based arc that is clamped by an alkyne tether was synthesized via Yamamoto coupling of dichloro precursor. DFT calculations (B3LYP/6‐31G*) indicate the lowest‐energy ground state adopts twisted, C 2 conformation bears 19.0 kcal/mol strain energy. X‐ray crystallographic analysis confirms that, in solid state, molecule twisted structure similar to calculated conformation. Exposure ortho ‐linked precursor conditions generates...
The Cover Feature shows a young archer carefully aiming his bow at target in the background. synthetic shown foreground incorporates short alkyne linker that clamps meta-quaterphenyl group, generating strain much like taut string creates tension an archer's bow. To illustrate this effect, cartoon threads through exterior benzene rings of quaterphenyl unit and tightens knot, drawing benzenes closer together. Photograph courtesy Alan Richard. More information can be found Full Paper by D. K....