1999

DOI: 10.1021/jo982014h

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Ozonolyses of 3-Benzoyloxy- and 3-Trimethylsiloxy-Substituted 2-Phenylindenes in Methanol: Substituent-Dependent Modes of Capture of the Carbonyl Oxide Intermediates by the Solvent

Kevin J. McCullough

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Cited by 6 publications

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The Structural Chemistry of Acyclic Organic Peroxides

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2009

Patai's Chemistry of Functional Groups

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Introduction Basic Principles Organic Peroxy Compounds Polyoxo Compounds Natural Products Concluding Remarks

The Structural Chemistry of Acyclic Organic Peroxides

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2009

Patai's Chemistry of Functional Groups

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Introduction Basic Principles Organic Peroxy Compounds Polyoxo Compounds Natural Products Concluding Remarks

Peroxycarbenium Ions as the “Gatekeepers” in Reaction Design: Assistance from Inverse Alpha‐Effect in Three‐Component β‐Alkoxy‐β‐peroxylactones Synthesis

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Chemistry A European J

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Stereoelectronic interactions control reactivity of peroxycarbenium cations, the key intermediates in (per)oxidation chemistry.C omputational analysis suggests that alcohol involvement as at hird component in the carbonyl/peroxide reactions remained invisible due to the absence of sufficiently deep kinetic traps neededt op reventt he escapeo f mixed alcohol/peroxidep roducts to the more stable bisperoxides.S ynthesis of b-alkoxy-b-peroxylactones, an ew type of organic peroxides, was accomplished by interrupting a thermodynamically driven peroxidation cascade. The higher energy b-alkoxy-b-peroxylactones do not transform into the more stable bisperoxides due to the stereoelectronically imposedi nstability of ac yclic peroxycarbenium intermediate as aconsequence of amplified inversea lpha-effect. The practical consequence of this fundamentalf inding is the first three-component cyclization/condensation of b-ketoesters, H 2 O 2 ,a nd alcohols that provides b-alkoxy-b-peroxylactones in 15-80 %yields.[a] Dr.

Pyrans and their Benzo Derivatives: Synthesis

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2008

Comprehensive Heterocyclic Chemistry III

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