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N ‐Methyl‐ C ‐(trichlortitanio)formimidoylchlorid. Ein effizientes Reagenz zur Homologisierung von Aldehyden und Ketonen zu α‐Hydroxy‐carbonsäureamiden
Author(s) -
Schiess Martin,
Seebach Dieter
Publication year - 1983
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.19830660531
Subject(s) - chemistry , acetophenone , reagent , titanium tetrachloride , medicinal chemistry , aldehyde , adduct , acetone , methylene , chloride , organic chemistry , ketone , titanium , catalysis
N ‐Methyl‐ C ‐(trichlorotitanio)formimidoyl Chloride, a Highly Efficient Reagent for Homologations of Aldehydes and Ketones to α‐Hydroxycarboxamides 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 90%, also with readily enolized ketones such as acetone and acetophenone. In contrast to the previously used organotitanium reagents of the type RTiX 3 , the preparation of the reagent 6 does not require any Li‐, Mg‐ or Zn‐derivative as a precusor.