In:
Chemistry – A European Journal, Wiley, Vol. 29, No. 50 ( 2023-09-06)
Abstract:
An exceptional level of control over the direction of the (2,3)‐sigmatropic rearrangement between N ‐oxides and alkoxylamine is achieved by simply changing the solvent in which they are dissolved. Protic solvents like water, methanol and hexafluoroisopropanol favour the N ‐oxide form, while other solvents like acetone, acetonitrile and benzene favour the alkoxylamine. The reaction temperature and nature of the substituents on the alkene affect the rate of rearrangement. A N ‐oxide fragment was attached to two fluorescent molecules and acted as an on/off switch for their fluorescence. The conversion of alkoxylamines into the corresponding N ‐oxides has not previously been described and is here termed the ‘Reverse Meisenheimer Rearrangement’.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.202301356
Language:
English
Publisher:
Wiley
Publication Date:
2023
detail.hit.zdb_id:
1478547-X
detail.hit.zdb_id:
1231884-X
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