Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes
Cis, syndiotactic A-alt-B copolymers, where A and B are two enantiomerically pure trans-2,3-disubstituted- 5,6-norbornenes with "opposite" chiralities, can be prepared with stereogenic-at-metal initiators of the type M(NR)- (CHR')(OR")(pyrrolide). Formation of a high percentage o...
| Main Authors: | , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Published: |
American Chemical Society (ACS)
2018
|
| Online Access: | http://hdl.handle.net/1721.1/113613 https://orcid.org/0000-0002-7405-6811 https://orcid.org/0000-0001-5827-3552 |
| _version_ | 1811097770875944960 |
|---|---|
| author | Jang, Eun Sil John, Jeremy M Schrock, Richard Royce |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Jang, Eun Sil John, Jeremy M Schrock, Richard Royce |
| author_sort | Jang, Eun Sil |
| collection | MIT |
| description | Cis, syndiotactic A-alt-B copolymers, where A and B are two enantiomerically pure trans-2,3-disubstituted- 5,6-norbornenes with "opposite" chiralities, can be prepared with stereogenic-at-metal initiators of the type M(NR)- (CHR')(OR")(pyrrolide). Formation of a high percentage of alternating AB copolymer linkages relies on an inversion of chirality at the metal with each propagating step and a relatively fast formation of an AB sequence as a consequence of a preferred diastereomeric relationship between the chirality at the metal and the chirality of the monomer. This approach to formation of an alternating AB copolymer contrasts dramatically with the principle of forming AB copolymers from achiral monomers and catalysts. |
| first_indexed | 2024-09-23T17:04:40Z |
| format | Article |
| id | mit-1721.1/113613 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T17:04:40Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1136132022-10-03T10:15:15Z Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes Jang, Eun Sil John, Jeremy M Schrock, Richard Royce Massachusetts Institute of Technology. Department of Chemistry Jang, Eun Sil John, Jeremy M Schrock, Richard Royce Cis, syndiotactic A-alt-B copolymers, where A and B are two enantiomerically pure trans-2,3-disubstituted- 5,6-norbornenes with "opposite" chiralities, can be prepared with stereogenic-at-metal initiators of the type M(NR)- (CHR')(OR")(pyrrolide). Formation of a high percentage of alternating AB copolymer linkages relies on an inversion of chirality at the metal with each propagating step and a relatively fast formation of an AB sequence as a consequence of a preferred diastereomeric relationship between the chirality at the metal and the chirality of the monomer. This approach to formation of an alternating AB copolymer contrasts dramatically with the principle of forming AB copolymers from achiral monomers and catalysts. United States. Department of Energy (DE-FG02- 86ER13564)0 2018-02-12T22:12:13Z 2018-02-12T22:12:13Z 2016-09 2016-07 2018-02-05T14:05:05Z Article http://purl.org/eprint/type/JournalArticle 2374-7943 2374-7951 http://hdl.handle.net/1721.1/113613 Jang, Eun Sil, Jeremy M. John, and Richard R. Schrock. “Synthesis of Cis,syndiotactic A-Alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes.” ACS Central Science 2, no. 9 (September 6, 2016): 631–636. © 2016 American Chemical Society https://orcid.org/0000-0002-7405-6811 https://orcid.org/0000-0001-5827-3552 http://dx.doi.org/10.1021/ACSCENTSCI.6B00200 ACS Central Science 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/pdf American Chemical Society (ACS) ACS |
| spellingShingle | Jang, Eun Sil John, Jeremy M Schrock, Richard Royce Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title | Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title_full | Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title_fullStr | Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title_full_unstemmed | Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title_short | Synthesis of Cis,syndiotactic A-alt-B Copolymers from Two Enantiomerically Pure Trans-2,3-Disubstituted-5,6-Norbornenes |
| title_sort | synthesis of cis syndiotactic a alt b copolymers from two enantiomerically pure trans 2 3 disubstituted 5 6 norbornenes |
| url | http://hdl.handle.net/1721.1/113613 https://orcid.org/0000-0002-7405-6811 https://orcid.org/0000-0001-5827-3552 |
| work_keys_str_mv | AT jangeunsil synthesisofcissyndiotacticaaltbcopolymersfromtwoenantiomericallypuretrans23disubstituted56norbornenes AT johnjeremym synthesisofcissyndiotacticaaltbcopolymersfromtwoenantiomericallypuretrans23disubstituted56norbornenes AT schrockrichardroyce synthesisofcissyndiotacticaaltbcopolymersfromtwoenantiomericallypuretrans23disubstituted56norbornenes |