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Article info. : 2006; 3(4) (pp 378~386)
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A Convenient Synthesis of Some α-Oxoketene-N,S-
and N,N-Acetals
H. Loghmani-Khouzani*, M.M. Sadeghi and M.H. Ghorbani
Department of Chemistry, Isfahan University, Isfahan
81746-73441, Iran
(Received 18 July 2006, Accepted 23 September2006)
Some α-oxoketene-N,S- and
N,N-acetals were selectively synthesized in good to excellent
yields by the reaction of 1,1-dimethoxy-4,4-di(methylthio)-3-buten-2-one
with primary and secondary amines under moderate conditions. Secondary
amines in reaction with α-oxoketene dithioacetal yielded
double-substitution products exclusively, whereas primary amines under
the same conditions yielded the mono-substituted products as exclusive
or main products.
Keywords:
Nucleophilic addition-elimination, α-Oxoketene dithioacetals, α-Oxoketene-N,
S-acetals, α-Oxoketene-N,N-acetals, Double-substitution |
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