Synthesis of activated alkenes bearing the difluoromethylenephosphonate group: a range of building blocks for the synthesis of secondary difluorophosphonates

Autor:	Thierry Lequeux, Afshan H. Butt, Howard J. Easterfield, G. Stuart Cockerill, Kevin Blades, Jonathan M. Percy
Rok vydání:	1999
Předmět:	Dephosphorylation chemistry.chemical_compound Nitroaldol reaction chemistry Organic chemistry Sulfoxide Methylene Hydrate Phosphate Nitroalkene E1cB-elimination reaction
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :3609-3614
ISSN:	1364-5463 0300-922X
DOI:	10.1039/a907052d
Popis:	Active methylene compounds reacted readily with stable hydrate 2-diethoxyphosphoryl-2,2-difluoroethane-1,1-diol to afford a range of activated alkenes bearing the difluoromethylenephosphonate group, a useful motif in the synthesis of phosphate ester mimics of biological interest. Wadsworth–Horner–Emmons reactions were employed using modified Rathke conditions for the syntheses of alkenoates, an alkenoic acid and a vinyl sulfone, while a Henry reaction followed by E1cB dehydration afforded an enedioate and a nitroalkene. A vinyl sulfoxide was less straightforward to synthesise and dephosphorylation to a difluoromethyl congener accompanied attempts to force the reaction to completion.
Databáze:	OpenAIRE
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