Uncommon 1,2-Migration of a Nitro Group Within a beta-Nitrostyryl Moiety: Synthetic Scope and Mechanistic Details

The unusual migration of a nitro group from the - to the -position of a -aryl--nitroethenyl moiety, following a nitrocyclopropane to isoxazoline N-oxide isomerization, has been studied from a mechanistic and synthetic points of view. As a result, two series of isomeric isoxazoline N-oxides could be obtained under controlled conditions. When reacted with diazomethane, a model transposed isoxazoline cleanly furnished a new, interesting pyrazolylisoxazole.


Published in:
European Journal Of Organic Chemistry, 2013, 28, 6298-6309
Year:
2013
Publisher:
Weinheim, Wiley-V C H Verlag Gmbh
ISSN:
1434-193X
Keywords:
Laboratories:




 Record created 2013-11-04, last modified 2018-01-28


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