Quantitative ring contraction of 5-hydroxy-1,3-oxazin-2-ones into 5-hydroxymethyl-1,3-oxazolidin-2-ones: A DFT study
The ring contraction of trans-5-hydroxy-1,3-oxazin-2-ones 1 into cis-5-hydroxymethyl-oxazolidinones 3 was studied with different bases and nucleophiles and it was found that it is the basicity and not the nucleophilicity the factor responsible for the ring contractions. A DFT study was made for the...
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Published in | Journal of molecular structure. Theochem Vol. 806; no. 1; pp. 141 - 144 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier B.V
31.03.2007
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Subjects | |
Online Access | Get full text |
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Summary: | The ring contraction of
trans-5-hydroxy-1,3-oxazin-2-ones
1 into
cis-5-hydroxymethyl-oxazolidinones
3 was studied with different bases and nucleophiles and it was found that it is the basicity and not the nucleophilicity the factor responsible for the ring contractions. A DFT study was made for the proposed mechanism. |
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ISSN: | 0166-1280 1872-7999 |
DOI: | 10.1016/j.theochem.2006.11.026 |