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Synthesis and structure of 2,4,6-tri-cyclo-butyl-1,3,5-trioxane.

ABSTRACT: The synthesis and structure of 2,4,6,-tri-cyclo-butyl-1,3,5-trioxane, C15H24O3 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclo-butyl-methanol and may serve as a stable precursor of the cyclo-butane carbaldehyde. The mol-ecule 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 cyclo-butane 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. Inter-molecular C-H?O inter-actions 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.

SUBMITTER: Shorunov SV

PROVIDER: S-EPMC6829721 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Synthesis and structure of 2,4,6-tri-cyclo-butyl-1,3,5-trioxane.

Shorunov Sergey V SV Bermeshev Maxim V MV Demchuk Dmitry V DV Nelyubina Yulia V YV

Acta crystallographica. Section E, Crystallographic communications 20191003 Pt 11

The synthesis and structure of 2,4,6,-tri-cyclo-butyl-1,3,5-trioxane, C15H24O3 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclo-butyl-methanol and may serve as a stable precursor of the cyclo-butane carbaldehyde. The mol-ecule 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 d ...[more]

PMID: 31709071

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