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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 |
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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. |
format | Online Article Text |
id | pubmed-6829721 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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