128258-85-5Relevant academic research and scientific papers
REACTION OF ACYL NITRENES WITH UNSATURATED COMPOUNDS VII. THE FORMATION OF STEREOISOMERIC 2-ARYL-2-OXAZOLINES DURING THE PHOTOLYSIS OF AROYL AZIDES IN cis- AND trans-1-METHOXY-1-PROPENES
Semenov, V. P.,Studenikov, A. N.,Ivanov, B. B.,Ogloblin, K. A.
, p. 278 - 281 (2007/10/02)
The irradiation of aroyl azides with UV light in the presence both of cis- and of trans-1-methoxy-1-propene in methylene chloride leads to the formation of a mixture of cis- and trans-4-methyl-5-methoxy-2-aryl-2-oxazolines containing up to 89percent of the trans isomer.Mixtures with larger contents of oxazolines having the trans configuration are formed from cis-1-methoxy-1-propene.According to the proposed mechanism, the isomerization of the intermediate 1-aroyl-2-methyl-3-methoxyaziridines takes place by a concerted mechanism with inversion of the migrating group and by a nonconcerted mechanism through a bipolar ion.
