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Über eine neuartige Basen‐katalysierte Umlagerung der Nitroso‐Gruppe
Author(s) -
Daeniker H. U.
Publication year - 1964
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.19640470107
Subject(s) - chemistry , acetonitriles , nitroso , nitrile , yield (engineering) , chemical transformation , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry , acetonitrile , materials science , metallurgy
By treatment with bases in methanolic solution N‐substituted N‐nitroso‐amino‐acetonitriles (I) undergo an internal rearrangement of the nitroso group to yield α‐isonitroso‐aminoacetonitriles (II). The structures of the rearrangement products are proved by their physico‐chemical properties, by chemical degradation to known products, and by transformation into a number of derivatives. Similar compounds in which the nitrile group of I is replaced by other activating groups do not rearrange to compounds analogous to 11, but lead in part to SCHIFF bases. Mechanisms for all these reactions are proposed.