Work

Self‐Assembly of a Trithioorthoformate‐Capped Cyclophane and Its Endohedral Inclusion of a Methine Group

Year: 2019

Type: article

Abstract: An unusual trithioorthoformate‐capped cyclophane cage was assembled via antimony‐activated iodine oxidation of thiols as confirmed by 1H‐NMR spectroscopy and X‐ray crystallography. The disulfide bridges can undergo desulfurization with hexamethylphosphorous triamide (HMPT) at ambient temperature to capture a trithioether cyclophane cage capped by the trithioorthoformate. In both cages a methine proton points directly into the small cavity. This unexpected structure is hypothesized to have formed as a result of haloform insertion during oxidation.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201903854

Authors: Mary S. Collins, Trevor A. Shear, Elizabeth K. Smith, S. Michael Strain, Lev N. Zakharov, Darren W. Johnson

Institution: University of Oregon

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science Foundation, Division of Chemistry, Integrative and Collaborative Education and Research

Awards: MRI: Acquisition of High Sensitivity 500 MHz NMR for the University of Oregon CAMCOR NMR Facility, Supramolecular Self-Assembly and Capture as a New Route to 3D Cyclophanes, G4189888121, G6393297082, Graduate Research Fellowship Program (GRFP)