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Diazoaldehyde Chemistry. Part 4 vilsmeier‐haack formylation of diazo compounds: A re‐investigation
Author(s) -
Sezer Özhan,
Dabak Kadir,
Anaç Olcay,
Akar Ahmet
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800327
Subject(s) - formylation , chemistry , diazo , yield (engineering) , reagent , medicinal chemistry , tetrafluoroborate , chloride , organic chemistry , catalysis , materials science , ionic liquid , metallurgy
Diazomethyl ketones (2‐diazoethanones) were reacted with the Vilsmeier reagent ((chloromethylidene)dimethylammonium chloride) to yield α‐diazo‐β‐oxoaldehydes and chloromethyl ketones. 2′,4′‐Dimethoxy‐α‐diazoacetophenone gave 2‐chloro‐1‐(2,4‐dimethoxyphenyl)‐3‐(dimethylamino)prop‐2‐en‐1‐one ( 5 ) in addition to the expected products. Phenyldiazomethanes gave the corresponding benzyl chlorides but not the (phenyl)diazoacetaldehydes even at temperatures as low as −60°. The diazo‐transfer reactions of phenylacetaldehydes and 2‐azido‐1‐ethylpyridin‐1‐ium tetrafluoroborate also did not yield the expected(phenyl)diazoacetaldehydes.