Little, M, Loughrey, J, Santoro, A et al. (2 more authors) (2014) Hexasulfanyl analogues of cyclotriveratrylene. Tetrahedron Letters, 55 (15). 2530 - 2533. ISSN 0040-4039
Abstract
The synthesis of four 3,4-di(alkylsulfanyl)benzyl alcohol derivatives is described, in five steps from methyl 3,4-di(hydroxy)benzoate via a Newman-Kwart rearrangement. Incubation of these derivatives in formic acid affords 2,3,7,8,12,13-hexakis(alkylsulfanyl)-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene products, which are hexa-sulfanyl analogues of the well-known supramolecular cavitand host, cyclotriveratrylene (CTV). The yield of this cyclization depends strongly on the alkylsulfanyl substituents present, in the order SMe > SEt ≈ SiPr ≫ SBn. A crystal structure determination of one of the cyclotrimers shows a mode of self-association that is commonly exhibited by CTV itself.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | (c) 2014, Elsevier. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, 55 (15), 2014, 10.1016/j.tetlet.2014.03.025 |
Keywords: | Cyclotriveratrylene; Thioether; Newman–Kwart rearrangement; Cavitand |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 12 Feb 2015 10:42 |
Last Modified: | 30 Jun 2020 14:49 |
Published Version: | http://dx.doi.org/10.1016/j.tetlet.2014.03.025 |
Status: | Published |
Publisher: | Elsevier |
Identification Number: | 10.1016/j.tetlet.2014.03.025 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:83006 |