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- Scopus: eid_2-s2.0-37049097955
- WOS: WOS:A1978FY45300025
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Article: Conformational behaviour of medium-sized rings. Part 5. Transannular reactions of (16z)-8,9-dihydro-8-methyl-7H-dinaphth- [1,8-cd:1',8'-hi]azacycloundecine and (12Z)-6,7-dihydro-6-methyl-5H-dibenz[c, g]azonine. Two examples of ‘reverse hofmann eliminations’
Title | Conformational behaviour of medium-sized rings. Part 5. Transannular reactions of (16z)-8,9-dihydro-8-methyl-7H-dinaphth- [1,8-cd:1',8'-hi]azacycloundecine and (12Z)-6,7-dihydro-6-methyl-5H-dibenz[c, g]azonine. Two examples of ‘reverse hofmann eliminations’ |
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Authors | |
Issue Date | 1978 |
Citation | Journal of the Chemical Society, Perkin Transactions 1, 1978, p. 1393-1398 How to Cite? |
Abstract | The olefinic double bonds in the cyclic ene-amines (5) and (8) have been shown to have the cis-configuration since two conformational diastereoisomers are formed in each case on quaternisation at nitrogen. The eleven-membered ring ene-amine (5). which is conformationally stable on the 1H n.m.r. time-scale up to +160 °C, undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic, neutral, and basic media. Although the nine-membered ring ene-amine (8). which is conformationally mobile on the 1H n.m.r. time-scale at room temperature, also undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic and neutral media, more vigorous reaction conditions are required. © 1978, Royal Society of Chemistry. |
Persistent Identifier | http://hdl.handle.net/10722/332790 |
ISSN | |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Brickwood, David J. | - |
dc.contributor.author | Hassan, Afaf M. | - |
dc.contributor.author | Ollis, W. David | - |
dc.contributor.author | Stephanatou, Julia Stephanidou | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:14:17Z | - |
dc.date.available | 2023-10-06T05:14:17Z | - |
dc.date.issued | 1978 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 1978, p. 1393-1398 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332790 | - |
dc.description.abstract | The olefinic double bonds in the cyclic ene-amines (5) and (8) have been shown to have the cis-configuration since two conformational diastereoisomers are formed in each case on quaternisation at nitrogen. The eleven-membered ring ene-amine (5). which is conformationally stable on the 1H n.m.r. time-scale up to +160 °C, undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic, neutral, and basic media. Although the nine-membered ring ene-amine (8). which is conformationally mobile on the 1H n.m.r. time-scale at room temperature, also undergoes transannular reactions involving the carbon-carbon double bond and the nitrogen atom in acidic and neutral media, more vigorous reaction conditions are required. © 1978, Royal Society of Chemistry. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the Chemical Society, Perkin Transactions 1 | - |
dc.title | Conformational behaviour of medium-sized rings. Part 5. Transannular reactions of (16z)-8,9-dihydro-8-methyl-7H-dinaphth- [1,8-cd:1',8'-hi]azacycloundecine and (12Z)-6,7-dihydro-6-methyl-5H-dibenz[c, g]azonine. Two examples of ‘reverse hofmann eliminations’ | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/P19780001393 | - |
dc.identifier.scopus | eid_2-s2.0-37049097955 | - |
dc.identifier.spage | 1393 | - |
dc.identifier.epage | 1398 | - |
dc.identifier.isi | WOS:A1978FY45300025 | - |