Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study
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چکیده
منابع مشابه
Regioselective oxidative ring opening of cyclopropyl silyl ethers: a quantum chemical study.
In contrast to the structurally and configurationally stable alkyl- or aryl-substituted cyclopropyl radical cations, cyclopropyl silyl ethers undergo spontaneous ring opening upon oxidation whereby the endocyclic C-C(O-TMS) bond is cleaved with remarkable selectivity. DFT calculations on 1-trimethylsilyloxybicyclo[4.1.0]heptane show that this selectivity arises from the topology of the potentia...
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Following previous work [J. Chem. Phys. 2013, 139, 154108] on a simple model of a reaction with a post-transition state valley ridge inflection point, we study the chemically important example of the electrocyclic cyclopropyl radical ring-opening reaction using direct dynamics and a reduced dimensional potential energy surface. The overall reaction requires con- or disrotation of the methylenes...
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A practical method for the synthesis of lycorine-type alkaloids with cis-B/C ring structure has been developed. Based on the reactions of aminocyclization, palladium-mediated arylation and especially cyclopropyl ring-opening rearrangement, the synthesis of anhydrocaranine, (±)-γ-lycorane and putative (±)-amarbellisine was accomplished.
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ژورنال
عنوان ژورنال: Chemistry - A European Journal
سال: 2010
ISSN: 0947-6539
DOI: 10.1002/chem.201000255