Preparation of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2– (trimethylsiloxy)propionate and Some Derivatives‐Molecular Structure of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2‐hydroxypropionate | Zendy

Schoth RalphMatthias | Zendy; Lork Enno | Zendy; Seifert Frank Uwe | Zendy; Breuer Eli | Zendy; Röschenthaler GerdVolker | Zendy

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Preparation of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2– (trimethylsiloxy)propionate and Some Derivatives‐Molecular Structure of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2‐hydroxypropionate

Author(s) -

Schoth RalphMatthias,

Lork Enno,

Seifert Frank Uwe,

Breuer Eli,

Röschenthaler GerdVolker

Publication year - 1997

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19971300222

Subject(s) - chemistry , propionate , phosphonate , trimethylsilyl , hydrolysis , tris , silylation , medicinal chemistry , propionates , stereochemistry , organic chemistry , catalysis , biochemistry

Methyl trifluoropyruvate ( 1 ) and tris(trimethylsilyl) phosphite ( 3 ) reacted to give methyl 2‐[bis(trimethylsiloxy)phosphoryl]‐ 3,3,3‐trifluoro‐2‐(trimethylsiloxy) propionate ( 4 ). Partial hydrolysis furnished propionate 6 , the molecular structure of which was obtained in the solid state. Attempted trimethylsilylation of the methylcarboxylato group in 4 using iodotrimethylsilane caused the formation of bis(trimethylsily1) [(2,2‐ difluoro‐ 1 ‐trimethylsiloxy)ethenyl]phosphonate ( 8 ). For comparison, methyl pyruvate ( 2 ) and 3 gave methyl 2‐[bis(trimethylsiloxy)phosphoryl]‐2‐(trimethylsiloxy)propionate ( 5 ).

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