(2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one

R Alan Aitken; Lynn Anita Power; Alexandra Martha Zoya Slawin

doi:10.3390/M1699

(2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one

R Alan Aitken^*, Lynn Anita Power, Alexandra Martha Zoya Slawin

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous workers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised.

Original language	English
Article number	M1699
Number of pages	5
Journal	Molbank
Volume	2023
Issue number	3
DOIs	https://doi.org/10.3390/M1699
Publication status	Published - 20 Jul 2023

Keywords

X-ray structure
Structural revision
Hydrogen bonding
1,3-dioxolan-4-one

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10.3390/M1699

Aitken-2023-Molbank-2023-M1699-CCBY
Copyright: © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/4.0/).
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title = "(2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one",

abstract = "The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous workers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised.",

keywords = "X-ray structure, Structural revision, Hydrogen bonding, 1,3-dioxolan-4-one",

author = "Aitken, {R Alan} and Power, {Lynn Anita} and Slawin, {Alexandra Martha Zoya}",

note = "Funding: The authors thank the School of Chemistry for a studentship to L.A.P.",

year = "2023",

month = jul,

day = "20",

doi = "10.3390/M1699",

language = "English",

volume = "2023",

journal = "Molbank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

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TY - JOUR

T1 - (2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one

AU - Aitken, R Alan

AU - Power, Lynn Anita

AU - Slawin, Alexandra Martha Zoya

N1 - Funding: The authors thank the School of Chemistry for a studentship to L.A.P.

PY - 2023/7/20

Y1 - 2023/7/20

N2 - The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous workers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised.

AB - The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous workers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised.

KW - X-ray structure

KW - Structural revision

KW - Hydrogen bonding

KW - 1,3-dioxolan-4-one

U2 - 10.3390/M1699

DO - 10.3390/M1699

M3 - Article

SN - 1422-8599

VL - 2023

JO - Molbank

JF - Molbank

IS - 3

M1 - M1699

ER -

(2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one

Abstract

Keywords

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