Synthesis of 2,6-Hexa-Tert-Butylterphenyl Derivatives, 2,6-(2,4,6-t-Bu₃C₆H₂)₂C₆H₃X, Where X = I, Li, OH, SH, N₃, or NH₂
Author(s)
Hoveyda, Amir H.
Bukhryakov, Konstantin
Schrock, Richard Royce
Mueller, Peter
Becker, Jonathan
Date Issued
May 2017
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Bukhryakov, Konstantin V. et al. “Synthesis of 2,6-Hexa-Tert-Butylterphenyl Derivatives, 2,6-(2,4,6-t-Bu₃C₆H₂)₂C₆H₃X, Where X = I, Li, OH, SH, N₃, or NH₂.” Organic Letters 19, 10 (May 2017): 2607–2609 © 2017 American Chemical Society
Version
Author's final manuscript
Abstract
A “double benzyne” reaction between 1,3-dichloro-2-iodobenzene and 2,4,6-t-Bu₃C₆H₂MgBr followed by the addition of iodine led to 2,6-(2,4,6-t-Bu₃C₆H₂)₂C₆H₃I (HTBTI) in 65% yield. Lithiation of HTBTI with Li-t-Bu gave Li(Et₂O)₂HTBT from which HTBTSH, HTBTN₃, HTBTNH₂, and HTBTOH were prepared. An X-ray structure of W(OHTBT)₂Cl₄ shows that the two HTBTO ligands are trans to one another with the t-Bu₃C6H₂ groups on one HTBTO interdigitated with the t-Bu₃C6H₂ groups on the other HTBTO.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/acs.orglett.7b01062
