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An unexpected base-induced [1,4]-phospho-Fries rearrangement

Mathieu Berchel 1 Jean-Yves Salaün 1 Hélène Couthon 1 Jean-Pierre Haelters 1 Paul-Alain Jaffres 1
1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
Abstract : An unexpected [1,4]-phospho-Fries rearrangement that gives rise to the formation of a O,O,O,O-tetraethyl methylenebis(thiophosphonate) derivative is reported. The regioselectivity of the metallation with n-BuLi or t-BuLi is the key factor that explains either the [1,4] or [1,3] rearrangement observed.
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https://hal.univ-brest.fr/hal-01577411
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Submitted on : Friday, August 25, 2017 - 3:40:28 PM
Last modification on : Thursday, November 29, 2018 - 4:09:17 PM

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Mathieu Berchel, Jean-Yves Salaün, Hélène Couthon, Jean-Pierre Haelters, Paul-Alain Jaffres. An unexpected base-induced [1,4]-phospho-Fries rearrangement. Dalton Transactions, Royal Society of Chemistry, 2010, 39 (47), ⟨10.1039/C0DT00880J⟩. ⟨hal-01577411⟩

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