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- W2126850394 abstract "Die baseinitiierte Umlagerung des 2,2,2-Trichlor-1-hydroxy-äthanphos-phonsäuredimethylesters (Trichlorphon) 1 führt in deuterierten Medien zu deuteriumfreiem O,O-Dimethyl-O-2,2-dichlorvinyl-phosphat (DDVP) 3. Dieser Befund stützt den von KHARASCH und BENGELSDORF vorgeschlagenen Reaktionsverlauf (Weg A: Umlagerung nach Deprotonierung der Hydroxylgruppe) und schließt einen später postulierten Mechanismus über das Enolphosphonat 5 als intermediärer DDVP-Vorstufe (Weg B) aus. In Einklang mit Weg A lassen sich auch C1-substituierte Trichlorphonderivate 12 in entsprechende Vinylphosphate 13 überführen. Kreuzungsexperimente belegen den intramolekularen Verlauf der Trichlorphon-DDVP-Umlagerung. Organic Phosphorus Compounds. IX. Studies on the Mechanism of the Trichlorphone-DDVP Rearrangement The base-initiated rearrangement of 2,2,2-trichloro-1-hydroxy-ethanephosphonic acid dimethyl ester (Trichlorphone) 1 in deuterated media leads to deuterium-free O, O-dimethyl O-2,2-dichlorovinyl phosphate (DDVP) 3. This result favours the course of reaction suggested by KHARASCH and BENGELSDORF (path A: rearrangement after deprotonation of the hydroxyl group) and rules out a mechanism via the enolphosphonate 5 as an intermediate DDVP-precursor (path B) as postulated later. In accordance with path A, C1-substituted Trichlorphone derivatives 12 can also be transformed to corresponding vinyl phosphates 13. Crossing experiments prove the intramolecular character of the Trichlorphone-DDVP rearrangement." @default.
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- W2126850394 date "1977-01-01" @default.
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- W2126850394 title "Organische Phosphorverbindungen. IX. Untersuchungen zum Mechanismus der Trichlorphon-DDVP-Umlagerung" @default.
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- W2126850394 doi "https://doi.org/10.1002/prac.19773190308" @default.
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