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Hexasulfanyl analogues of cyclotriveratrylene

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Volume
55
Issue
15
Identifiers
DOI: 10.1016/j.tetlet.2014.03.025
Keywords
  • Cyclotriveratrylene
  • Thioether
  • Newman–Kwart Rearrangement
  • Cavitand

Abstract

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.

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