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- W2016249989 abstract "In aprotischen Solventien wie Tetrahydrofuran, Chloroform, Benzol, Aceton oder Dimethyl-formamid isomerisieren sich Methyl-benzyl-phenacyl-sulfoniumylide 8 unter 1.2-Benzyl-Wanderung zu den Sulfiden 5. Daneben entstehen 2.3-Dimethylmercapto-1.4-diphenyl-butandion-(l.4) (9) und Dibenzyle. In Methanol oder Wasser isomerisieren sich demgegenüber die Ylide 8 ausschließlich bzw. hauptsächlich zu Enoläthern vom Typ 6. - Die Geschwindigkeit der l .2-Verschiebung wird durch Substituenten im wandernden Benzyl-Rest nur geringfügig beeinflußt. 5a zeigt unmittelbar nach der Isomerisation eine chemisch induzierte Proton-Spinpolarisation. Für die Umlagerung wird ein Spaltungs-Rekombinations-Mechanismus mit dem Radikalpaar 12 als Zwischenstufe angenommen. - Das unterschiedliche Verhalten von 8 in aprotischen und protischen Solventien wird diskutiert. 1,2-Migrations to the Atom with Free Electron Pair, IX1). Evidence for a Radical Mechanism of the 1,2-Benzyl-migration in the Isomerisation of Methyl-benzyl-phenacyl-sulfonium-ylides2) In aprotic solvents such as tetrahydrofurane, chloroform, benzene, acetone, or dimethyl-formamide the title compounds 8 isomerize to the sulfides 5. In addition, 2,3-dimethylmercapto-l,4-diphenyl-1,4-butanedione (9) as well as dibenzyls are formed. In methanol or water the ylides isomerize exclusively or primarily to enol ethers of type 6. - The rate of the 1,2-shift is hardly influenced by substituents in the migrating benzyl group. Immediately after isomerization 5a shows chemically induced proton spin polarization. The rearrangement is assumed to go by way of a cleavage-recombination-mechanism with the intermediary radical pair 12. - The different behavior of 8 in aprotic and protic solvents is discussed." @default.
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- W2016249989 title "1.2-Wanderungen zum Atom mit freiem Elektronenpaar, IX1) Hinweise auf den radikalischen Ablauf der 1.2-Benzyl-Wanderung bei der Isomerisation von Methyl-benzyl-phenacyl-sulfoniumyliden2)" @default.
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