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
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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.
Date issued
2017-05Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
1523-7060
1523-7052