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- Publisher Website: 10.1021/ja00245a034
- Scopus: eid_2-s2.0-0000238049
- WOS: WOS:A1987H545500034
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Article: Conformational Cycloenantiomerism in l,2-Bis(l-bromoethyl)-3,4,5,6-tetraisopropylbenzene
Title | Conformational Cycloenantiomerism in l,2-Bis(l-bromoethyl)-3,4,5,6-tetraisopropylbenzene |
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Authors | |
Issue Date | 1987 |
Citation | Journal of the American Chemical Society, 1987, v. 109, n. 11, p. 3397-3402 How to Cite? |
Abstract | The concept of cycloenantiomerism is critically reexamined. It is shown that suitably substituted derivatives of hexaisopropylbenzene (1) illustrate a novel type of stereoisomerism, in which enantiomers are distinguished by the sense of conformational orientation of side chains for a given configurational distribution pattern of stereocenters. Such isomers, which may be described as conformational cycloenantiomers, have now been synthesized for the first time. Photobromination of l,2-diethyl-3,4,5,6-tetraisopropylbenzene yields a mixture of the two diastereomeric l,2-bis(l-bromoethyl)-3,4,5,6-tetraiso-propylbenzenes (2), from which the (1'RS,2'SR) isomer (2a) is isolated by HPLC. This isomer is a racemic mixture of conformational cycloenantiomers. VT-NMR measurements yield a lower limit of AG* = 24 kcal mol-1for the enantiomerization of 2a. © 1987, American Chemical Society. All rights reserved. |
Persistent Identifier | http://hdl.handle.net/10722/341438 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Singh, M. Dhaneshwar | - |
dc.contributor.author | Siegel, Jay | - |
dc.contributor.author | Biali, Silvio E. | - |
dc.contributor.author | Mislow, Kurt | - |
dc.date.accessioned | 2024-03-13T08:42:49Z | - |
dc.date.available | 2024-03-13T08:42:49Z | - |
dc.date.issued | 1987 | - |
dc.identifier.citation | Journal of the American Chemical Society, 1987, v. 109, n. 11, p. 3397-3402 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341438 | - |
dc.description.abstract | The concept of cycloenantiomerism is critically reexamined. It is shown that suitably substituted derivatives of hexaisopropylbenzene (1) illustrate a novel type of stereoisomerism, in which enantiomers are distinguished by the sense of conformational orientation of side chains for a given configurational distribution pattern of stereocenters. Such isomers, which may be described as conformational cycloenantiomers, have now been synthesized for the first time. Photobromination of l,2-diethyl-3,4,5,6-tetraisopropylbenzene yields a mixture of the two diastereomeric l,2-bis(l-bromoethyl)-3,4,5,6-tetraiso-propylbenzenes (2), from which the (1'RS,2'SR) isomer (2a) is isolated by HPLC. This isomer is a racemic mixture of conformational cycloenantiomers. VT-NMR measurements yield a lower limit of AG* = 24 kcal mol-1for the enantiomerization of 2a. © 1987, American Chemical Society. All rights reserved. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Conformational Cycloenantiomerism in l,2-Bis(l-bromoethyl)-3,4,5,6-tetraisopropylbenzene | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja00245a034 | - |
dc.identifier.scopus | eid_2-s2.0-0000238049 | - |
dc.identifier.volume | 109 | - |
dc.identifier.issue | 11 | - |
dc.identifier.spage | 3397 | - |
dc.identifier.epage | 3402 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:A1987H545500034 | - |