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Original Articles

α-SUBSTITUIERTE PHOSPHONATE 62.1 TRIETHOXYPHOSPHONIUM-YLIDE BZW.-BETAINE AUS TRIETHYLPHOSPHIT UND 7-PHOSPHORYLCHINONMETHIDEN, SYNTHESE UND REAKTIVITÄT

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Pages 331-337 | Received 07 Apr 1992, Published online: 26 May 2009
 

Abstract

Durch Addition von Triethylphosphit (TEP) an die 7-Diethylphosphono- bzw. 7-Diphenylphosphinyl-3,5-di-tert.-butyl-chinonmethide 4a,b entstehen nicht die erwarteten Phosphonium-betaine 13a,b son-dern unter Protonenwanderung die überraschend stabilen Triethoxyphosphonium-ylide 14a,b. Das aus TEP und 7,7-Bisphosphonochinonmethid 6a erwartete Phosphoniumbetain 18 war unstabil und gab sofort unter Ethylenabspaltung und Protonentransfer das 4-Hydroxyaryl-trisphosphonat 7.

By addition of triethylphosphit (TEP) to the 7-diethylphosphono- or 7-diphenylphosphinyl-3,5-di-tert.-butyl-quinone methides 4a,b are formed by proton transfer, the surprisingly stable triethoxyphosphonium ylides 14a,b and not the expected phosphonium-betaines 13a,b. The phosphonium betain 18, which was expected from the reaction of TEP and the 7,7-bisphosphono-quinone methide 6a, was unstable and decomposed by proton transfer and splitting off ethylen to the 4-hydroxyaryl-trisphosphonate 7.

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