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
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-ra...
| Main Authors: | , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
American Chemical Society (ACS)
2018
|
| Online Access: | http://hdl.handle.net/1721.1/115127 https://orcid.org/0000-0001-5827-3552 https://orcid.org/0000-0001-6530-3852 |
| _version_ | 1826200411775696896 |
|---|---|
| author | Hoveyda, Amir H. Bukhryakov, Konstantin Schrock, Richard Royce Mueller, Peter Becker, Jonathan |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Hoveyda, Amir H. Bukhryakov, Konstantin Schrock, Richard Royce Mueller, Peter Becker, Jonathan |
| author_sort | Hoveyda, Amir H. |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T11:35:59Z |
| format | Article |
| id | mit-1721.1/115127 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:35:59Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1151272022-04-01T20:12:51Z 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 Hoveyda, Amir H. Bukhryakov, Konstantin Schrock, Richard Royce Mueller, Peter Becker, Jonathan Massachusetts Institute of Technology. Department of Chemistry Schrock, Richard Royce Bukhryakov, Konstantin Schrock, Richard Royce Mueller, Peter Becker, Jonathan 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. National Institutes of Health (U.S.) (Award GM-59426) 2018-05-01T15:13:33Z 2018-05-01T15:13:33Z 2017-05 2017-04 Article http://purl.org/eprint/type/JournalArticle 1523-7060 1523-7052 http://hdl.handle.net/1721.1/115127 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 https://orcid.org/0000-0001-5827-3552 https://orcid.org/0000-0001-6530-3852 en_US http://dx.doi.org/10.1021/acs.orglett.7b01062 Organic Letters 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. application/octet-stream American Chemical Society (ACS) Prof. Schrock via Erja Kajosalo |
| spellingShingle | Hoveyda, Amir H. Bukhryakov, Konstantin Schrock, Richard Royce Mueller, Peter Becker, Jonathan 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| url | http://hdl.handle.net/1721.1/115127 https://orcid.org/0000-0001-5827-3552 https://orcid.org/0000-0001-6530-3852 |
| work_keys_str_mv | AT hoveydaamirh synthesisof26hexatertbutylterphenylderivatives26246tbu3c6h22c6h3xwherexiliohshn3ornh2 AT bukhryakovkonstantin synthesisof26hexatertbutylterphenylderivatives26246tbu3c6h22c6h3xwherexiliohshn3ornh2 AT schrockrichardroyce synthesisof26hexatertbutylterphenylderivatives26246tbu3c6h22c6h3xwherexiliohshn3ornh2 AT muellerpeter synthesisof26hexatertbutylterphenylderivatives26246tbu3c6h22c6h3xwherexiliohshn3ornh2 AT beckerjonathan synthesisof26hexatertbutylterphenylderivatives26246tbu3c6h22c6h3xwherexiliohshn3ornh2 |