Alkylation of Esters and Ketones with Nitroethylene
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Authors
Buzby, Jennifer C.
Issue Date
1999
Type
Thesis
Language
en_US
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Abstract
Nitroethylene is a potentially useful "+CH2CH2NH2" synthon that has not been widely
used in conjugate addition reactions, due in part to its reputation for facile anionic
polymerization. This paper reports a systematic study of the scope and limitations of the
conjugate addition of ketone and esters to nitroethylene. Synthetically useful yields are reported
for both esters and ketone lithium enolates of a variety of structural types. It was found that amonosubstituted
ester and ketones enolates produced higher yields of addition products than
their a-disubstituted counterparts. Substitution of the I3-carbon also improved yields in ester
enolates.
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