Hexasulfanyl analogues of cyclotriveratrylene |
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Authors: | Marc A Little Jonathan J Loughrey Amedeo Santoro Malcolm A Halcrow Michaele J Hardie |
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Institution: | School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK |
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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-tribenzoa,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. |
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Keywords: | Cyclotriveratrylene Thioether Newman&ndash Kwart rearrangement Cavitand |
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