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Synthesis and structure of 2,4,6-tricyclobutyl-1,3,5-trioxane
The synthesis and structure of 2,4,6,-tricyclobutyl-1,3,5-trioxane, C(15)H(24)O(3) 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclobutylmethanol and may serve as a stable precursor of the cyclobutane carbaldehyde. The molecule of 1 occupies a speci...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829721/ https://www.ncbi.nlm.nih.gov/pubmed/31709071 http://dx.doi.org/10.1107/S205698901900896X |
Sumario: | The synthesis and structure of 2,4,6,-tricyclobutyl-1,3,5-trioxane, C(15)H(24)O(3) 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclobutylmethanol and may serve as a stable precursor of the cyclobutane carbaldehyde. The molecule of 1 occupies a special position (3.m) located at the center of its 1,3,5-trioxane ring. The latter is in a chair conformation, with the symmetry-independent O and C atoms deviating by 0.651 (4) Å from the least-squares plane of the other atoms of the trioxane ring. All three cyclobutane substituents, which have a butterfly conformation with an angle between the two planes of 25.7 (3)°, are in the cis conformation relative to the 1,3,5-trioxane ring. Intermolecular C—H⋯O interactions between the 1,3,5-trioxane rings consolidate the crystal structure, forming stacks along the c-axis direction. The crystal studied was refined a as a racemic twin. |
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