An efficient method for α-monofluorination of carbonyl compounds with molecular fluorine: Use of α-hydroxymethylene substituent as directing and activating groups
Molecular fluorine efficiently reacts with α-hydroxymethylene carbonyl compounds to give α-fluoro-α-formyl compounds in a highly site-specific manner. The fluorinated compounds mostly isolated as their hemiacetals with methanol are readily deformylated just by treatment with weak bases affording α-monofluorinated carbonyl compounds. In this fluorination method, the hydroxymethylene group serves not only as a directing group but also as the activating group of carbonyl compounds for fluorination. By this method, a series of α-fluoro carbonyl compounds including esters was synthesized in high yields.
Kamaya, Hiroshi,Sato, Masayuki,Kaneko, Chikara
p. 587 - 590
(2007/10/03)
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