Premium
Eine neue Version der Epoxyketon → Alkinon‐Fragmentierung: Thermischer Zerfall der Hydrazone aus α,β‐Epoxycarbonyl‐verbindungen und N‐Amino‐aziridinen. Vorläufige Mitteilung
Author(s) -
Felix Dorothee,
Schreiber J.,
Piers K.,
Horn U.,
Eschenmoser A.
Publication year - 1968
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.19680510632
Subject(s) - chemistry , hydrazone , medicinal chemistry , acetophenone , phenylglyoxal , aziridine , yield (engineering) , stereochemistry , organic chemistry , amino acid , ring (chemistry) , materials science , metallurgy , catalysis , biochemistry , arginine
A new version of the epoxyketone → alkynone fragmentation is described. Hydrazones derived from cyclic α,β‐epoxy‐ketones and N‐amino‐aziridines decompose thermally into molecular nitrogen, an olefinic fragment and an acetylenic carbonyl compound (compare scheme 1). The reaction of phenylglyoxal with N‐amino‐phenyl‐aziridine at room temperature produces styrene and diazo‐acetophenone in high yield (compare scheme 3).