Thermische umlagerung von quadratsäure-bis(trimethylsilyl)ester

Reetz, Manfred T.; Neumeier, G.; Kaschube, M.

doi:10.1016/s0040-4039(00)72653-0

Cited by 16 publications

(5 citation statements)

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“…Alternatively, more extended π-systems 264 can rearrange to unsaturated compounds 267 , either through concerted mechanisms involving transition structures such as 265 or through stepwise mechanisms involving zwitterionic species of type 266 (Scheme , paths (b) and (c), respectively). Dyotropic reactions involving (trialkylsiloxy)enones belong formally to the transformation reported in Scheme B, although no computational studies on the reaction mechanisms of these rearrangements have been reported to date.…”

Section: Theoretical and Computational Studies On Reaction Mechanismsmentioning

confidence: 99%

Dyotropic Reactions: Mechanisms and Synthetic Applications

2009

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Israel Ferna ´ndez (Madrid, 1977) enjoyed studying chemistry at the Universidad Complutense of Madrid (UCM). In 2005, he earned his Ph.D. in Chemistry at the UCM under the supervision of Prof. Miguel A. Sierra and received the Prize for the best Doctoral Thesis in Synthetic Chemistry by the Spanish Royal Society of Chemistry and the Lilly-Young Researcher Prize. After that, he joined the Theoretical and Computational Chemistry group of Prof. G. Frenking at the Philipps Universita ¨t Marburg as a postdoctoral researcher studying the bonding situation and reaction mechanisms of organic and organometallic compounds. At the present, I.F. is a Ramo ´n y Cajal fellow at the UCM. His current research includes the computational study of the bonding situation and reaction mechanisms of organic, organometallic, and bioorganic compounds with special interest in C-C bond forming processes.

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Section: Theoretical and Computational Studies On Reaction Mechanismsmentioning

confidence: 99%

Dyotropic Reactions: Mechanisms and Synthetic Applications

2009

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“…In this context a paper should be mentioned (Reetz er al. [7]) in which a fast isomerization of bis(trimethy1-silyl) squarate at T>80" is reported. The process is intermolecular and results in an averaging of the two types of ring carbon atoms.…”

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confidence: 99%

¹³C‐NMR. Spectra, Structure and Reactivity of Cyclic Oxocarbons

Städeli

Hollenstein

Philipsborn

1977

Helvetica Chimica Acta

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SummaryThe structures of cyclic polyketones, their hydrates and reduction products were studied in different solvents by 13C-NMR. spectroscopy. In dimethylsulfoxide solution rhodizonic acid (l), croconic acid (2) and squaric acid (3) exhibit signal averaging. In anhydrous tetrahydrofuran 1 and 2 could be observed as non-dynamic species. The spontaneous reactions of dodecahydroxycyclohexane (5) and decahydroxycyclopentane ('leuconic acid') (6) and the sequence of formation of ring-contracted products were investigated. Key intermediates could be clearly identified which support the mechanism proposed earlier involving a benzylic acid type rearrangement followed by decarboxylation and subsequent redox reactions.

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“…Upon standing, the 1 : 1 molar mixture of Va and its D l8 -derivative Vc at room temperature, a statistical 1 : 1 : 2 distribution of isotopomeric compounds Va, c, d was rapidly achieved, as has been demonstrated by mass spectroscopy [8]. Upon standing, the 1 : 1 molar mixture of Va and its D l8 -derivative Vc at room temperature, a statistical 1 : 1 : 2 distribution of isotopomeric compounds Va, c, d was rapidly achieved, as has been demonstrated by mass spectroscopy [8].…”

Section: Concerted and Nonconcerted Dyotropic Rearrangementsmentioning

confidence: 75%