ChemInform Abstract: Synthesis of Activated Alkenes Bearing the Difluoromethylenephosphonate Group: A Range of Building Blocks for the Synthesis of Secondary Difluorophosphonates

Autor:	Kevin Blades, Afshan H. Butt, Howard J. Easterfield, Jonathan M. Percy, G. Stuart Cockerill, Thierry Lequeux
Rok vydání:	2010
Předmět:	Elimination reaction chemistry.chemical_compound Nitroaldol reaction Chemistry Organic chemistry Sulfoxide General Medicine Methylene Nitroalkene Phosphate Hydrate E1cB-elimination reaction
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e160a385a4fd15bc5a93a26caf0c5290 https://doi.org/10.1002/chin.200016166 Zobrazit plný text záznamu Plný text