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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...

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Autores principales: Shorunov, Sergey V., Bermeshev, Maxim V., Demchuk, Dmitry V., Nelyubina, Yulia V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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
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author Shorunov, Sergey V.
Bermeshev, Maxim V.
Demchuk, Dmitry V.
Nelyubina, Yulia V.
author_facet Shorunov, Sergey V.
Bermeshev, Maxim V.
Demchuk, Dmitry V.
Nelyubina, Yulia V.
author_sort Shorunov, Sergey V.
collection PubMed
description 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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spelling pubmed-68297212019-11-08 Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane Shorunov, Sergey V. Bermeshev, Maxim V. Demchuk, Dmitry V. Nelyubina, Yulia V. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2019-10-03 /pmc/articles/PMC6829721/ /pubmed/31709071 http://dx.doi.org/10.1107/S205698901900896X Text en © Shorunov et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Shorunov, Sergey V.
Bermeshev, Maxim V.
Demchuk, Dmitry V.
Nelyubina, Yulia V.
Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title_full Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title_fullStr Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title_full_unstemmed Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title_short Synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
title_sort synthesis and structure of 2,4,6-tri­cyclo­butyl-1,3,5-trioxane
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829721/
https://www.ncbi.nlm.nih.gov/pubmed/31709071
http://dx.doi.org/10.1107/S205698901900896X
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