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 inJournal of molecular structure. Theochem Vol. 806; no. 1; pp. 141 - 144
Main Authors Hamdach, A., Zaragozá, R.J., Zaballos-García, E., Sepúlveda-Arques, J.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 31.03.2007
Subjects
1,3-Oxazin-2-ones
1,3-Oxazolidin-2-ones
DFT study
Ring contraction
1,3-Oxazolidin-2-ones
1,3-Oxazin-2-ones
Ring contraction
DFT study
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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.
ISSN:0166-1280
1872-7999
DOI:10.1016/j.theochem.2006.11.026