155. N-Methyl-C-(trichlortitanio)formimidoylchlorid. Ein effizientes Reagenz zur Homologisierung von Aldehyden und Ketonen zu α-Hydroxy-carbonsaeureamiden

Article abstract of DOI:10.1002/hlca.19830660531

The known title compound 6 formed by addition of titanium tetrachloride to methyl isocyanide in methylene chloride adds to the carbonyl group of aldehydes and ketones.The adducts 7 are hydrolized to N-methyl-α-hydroxycarboxamides 8 which are (from ketones) or are not branched (from aldehydes) in the α-position.The yields in this new modification of the Passerini reaction are near 90percent, also with readily enolized ketones such as acetone and acetophenone.In contrast to the previously used organotitanium reagents of the type RTiX3, the preparation of the reagent 6 does not require any Li-, Mg- or Zn-derivative as a precursor.