Synthesis and structures of O-anthrylmethyl-substituted hexahomotrioxacalix[3]arenes

Jiang, Xue-Kai; Ikejiri, Yusuke; Ni, Xi-Long; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

Abstract

O-Alkylation of 7,15,23-tri-tert-butyl-25,26,27-trihydroxy-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene (1H₃) with 9-chloromethylanthracene 5 was carried out under different reaction conditions. Variation of the number of anthrylmethyl group introduced at the phenolic rim of hexahomotrioxacalix[3]arene 1H₃ was achieved through selective O-alkylation using stoichiometric amounts of 9-chloromethylanthracene 5 in acetone to afford the mono-O-alkylated product 2H₂An, the di-O-alkylated product 3HAn₂ and the tri-O-alkylated product partial-cone-4An₃, respectively. Interestingly, by using an acetone/benzene (1:1 v/v) mixed solvent system, the cone-4An₃ was successfully synthesized. These results suggest that the solvent can also control the conformation of the O-alkylation products. The possible reaction routes of the cone-4An₃ and partial-cone-4An₃ are also discussed.

Citation

Jiang, X.-K., Ikejiri, Y., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2016). Synthesis and structures of O-anthrylmethyl-substituted hexahomotrioxacalix[3]arenes. Journal of molecular structure, 1120, 274-280. https://doi.org/10.1016/j.molstruc.2016.05.020

• Journal Article Type: Article
• Acceptance Date: May 9, 2016
• Online Publication Date: May 11, 2016
• Publication Date: Sep 15, 2016
• Deposit Date: Jun 21, 2016
• Publicly Available Date: Jun 21, 2016
• Journal: Journal of molecular structure
• Print ISSN: 0022-2860
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 1120
• Pages: 274-280
• DOI: https://doi.org/10.1016/j.molstruc.2016.05.020
• Keywords: Homotrioxacalix[3]arenes, Selective O-alkylation, Solvent effects, Conformation
• Public URL: https://hull-repository.worktribe.com/output/439966
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0022286016304677
• Additional Information: This article is maintained by: Elsevier; Article Title: Synthesis and structures of O-anthrylmethyl-substituted hexahomotrioxacalix[3]arenes; Journal Title: Journal of Molecular Structure; CrossRef DOI link to publisher maintained version: http://dx.doi.org/10.1016/j.molstruc.2016.05.020; Content Type: article; Copyright: © 2016 Elsevier B.V. All rights reserved.
• Contract Date: Jun 21, 2016