A ONE-POT SYNTHESIS OF UNSYMMETRICAL AND SYMMETRICAL TETRASUBSTITUTED α-FLUORO-α,β-UNSATURATED ESTERS

A ONE-POT SYNTHESIS OF UNSYMMETRICAL AND SYMMETRICAL TETRASUBSTITUTED α-FLUORO-α,β-UNSATURATED ESTERS

Acylation of [(EtO) 2 P(O)CFCO 2 Et] − Li + 1 with acid chlorides RC(O)Cl or phosgene ClC(O)Cl and subsequent reaction of the acylated phosphonate with organometallic reagents (R'M) provide unsymmetrical and symmetrical tetrasubstituted α-fluoro-α,β-unsaturated esters, RR'C=CFCO 2 Et and R...

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Veröffentlicht in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1995-08, Vol.105 (1-4), p.205-212
Hauptverfasser: Tsai, Hou-Jen, Thenappan, Alagappan, Burton, Donald J.
Format: Artikel
Sprache:eng
Schlagworte:
betaine
Emmons reaction
olefins
perfluorinated Grignard reagents
phosgene
β-ketophosphonates
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Zusammenfassung:Acylation of [(EtO) 2 P(O)CFCO 2 Et] − Li + 1 with acid chlorides RC(O)Cl or phosgene ClC(O)Cl and subsequent reaction of the acylated phosphonate with organometallic reagents (R'M) provide unsymmetrical and symmetrical tetrasubstituted α-fluoro-α,β-unsaturated esters, RR'C=CFCO 2 Et and R' 2 C=CFCO 2 Et, in moderate to good yields.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509508042064