Author:
Baxter GJ,Brown RFC,Eastwood FW,Gatehouse BM,Nesbit MC
Abstract
Isopropylideneketene
(3-methylbuta-1,2-dien-1-one), Me2C=C=C=O, reacts with ketene and
substituted ketenes to give oxetanones or cyclobutane-1,3-diones formed by
[2+2] cycloadditions involving the central C=C bond of the methyleneketene. By
contrast Me2C=C=C=O reacts with 5,5- dimethylpyrroline
1-oxide to give a spirooxazolidinone (13) and an oxetanone (17), both of which
appear to be formed by initial cycloaddition of the pyrroline 1-oxide to the
terminal C=C bond of the methyleneketene and formation of an intermediate
bicyclic ketene (15). The structure of the oxetanone (17) has been confirmed
and its stereochemistry established by X-ray crystallography.
Cited by
14 articles.
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