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Nitrosoalkenes: Synthesis and Reactivity
Author(s) -
Francotte Eric,
Merényi Robert,
VandenbulckeCoyette Brigitte,
Viehe HeinzGünther
Publication year - 1981
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.19810640425
Subject(s) - chemistry , cycloaddition , oxime , reactivity (psychology) , halogen , alkoxy group , medicinal chemistry , group (periodic table) , stereochemistry , organic chemistry , catalysis , alkyl , medicine , alternative medicine , pathology
Some α‐ and β‐halonitrosoalkenes 1 have been synthesized and characterized. The halogen atoms of the oxime precursors 2 can be substituted by alkoxy groups. Two kinds of cycloaddition reaction of 1 have been observed: (i) reaction of the NO group with dienes gives 3, 6‐dihydrooxazine derivatives 6 which isomerise to epoxyepimines 7 in most cases of β‐substituted nitrosoalkenes; (ii) if 4, 5‐dihydrooxazines 22 are obtained, the cycloaddition of the nitrosoalkenes as 4π‐component is presumed.

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