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2,2-difluoro-1-tosyloxyvinyllithium: a novel, effective reagent for the preparation of α-keto acids from carbonyl compounds

✍ Scribed by Kiyoshi Tanaka; Takeshi Nakai; Nobuo Ishikawa

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 130 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85738-5

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✦ Synopsis

Carbanions stabilized by8-fluorine atom(s) are the most frequently encountered intermediates in organofluorine reactions and hence may serve as nucleophiles in carbon-carbon No. L@ Table I. Synthesis ofa-Keto Acids (2) Carbonyl Acid @ Compound Yield,Th d-Keto Acid? Yield,%k Mp,"C (Lit.) Acetone (CH,),CHCOCOOH 95 (57C) Oild J L Cyclohexanone 76 0 COCOOH 91 48-49 (45-4ge) Z-Butanone 6s 7lh CH3CH2QICOOH 92 39-40 (409) n-Heptanal CH3(CH2)6COCOOH 98 43-44 (43-441) Benzaldehyde 781 PhCH2COCOOH-j-89 154-1;Ec (VXc k) Crotonaldehyde 7+ 1 CA11 products exhibited spectral (ir and nmr) data in accord with the assigned structures. b -Isolated yields based on ,l_ and $for f?. and 2, respectively. c Overall yield based on J by the one-step procedure (see text). d Its 2,4_dinitrophenylhydrazone, mp, 197-198°C [lit. mp, 197"C:

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