ISSN:
1573-9171
Keywords:
dialkoxyaminyl biradicals
;
2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine
;
dialkoxydiazene oxides
;
conformation
;
inversion
;
x-ray structure analysis
;
stereoelectronic control
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The oxidation of 1,2-bis(methoxyaminooxy)ethane (3) with PbO2 afforded 2,3-dimethoxyperhydro-1,4,2,3-dioxadiazine (4) in the form of the 55:45 mixture of thetrans-4ee- andcis-4 isomers. The barrier of the ring conversion (ΔG238 ≠=11.3 kcal/mole) of thecis-4 isomer was determined by the method of13C NMR. The regio- and stereospecific stereoelectronically controlled reaction of (4) withpara-nitrobenzoic acid gives the equimolar mixture of methylpara-nitrobenzoate and the 1,2-dialkoxydiazene oxide (5), the structure of which, and the (E)-configuration, were shown by the x-ray structural data of its acylation product — the diazene oxide (6).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00863376
Permalink