Synthesis and structure of 2,4,6-tri-cyclo-butyl-1,3,5-trioxane
| Autor: | Dmitry V. Demchuk, Yulia V. Nelyubina, Maxim V. Bermeshev, S. V. Shorunov |
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| Rok vydání: | 2019 |
| Předmět: |
cyclobutane
crystal structure Trioxane Cyclohexane conformation Crystal structure 010402 general chemistry Ring (chemistry) 01 natural sciences trioxane cyclobutane carbaldehyde Cyclobutane Research Communications Crystal lcsh:Chemistry chemistry.chemical_compound cyclobutane carbaldehyde swern oxidation Swern oxidation General Materials Science 010405 organic chemistry Chemistry General Chemistry Condensed Matter Physics 1 3 5-Trioxane 0104 chemical sciences Crystallography lcsh:QD1-999 strained rings cyclobutane |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 75, Iss 11, Pp 1578-1581 (2019) Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| Popis: | The synthesis and structure of the substituted trioxane compound 2,4,6,-tricyclobutyl-1,3,5-trioxane is described. The three cyclobutane rings attached to the 1,3,5-trioxane six-membered ring are all in a cis arrangement. The compound may find application as a stable trimeric form of the fragile cyclobutane carbaldehyde. The synthesis and structure of 2,4,6,-tricyclobutyl-1,3,5-trioxane, C15H24O3 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. |
| Databáze: | OpenAIRE |
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