Interaction, bond formation or reaction between a dimethylamino group and an adjacent alkene or aldehyde group in aromatic systems controlled by remote molecular constraints

Bristow, J.C., Cliff, S.V.A., Yang, S. and Wallis, J.D. ORCID: 0000-0001-7259-8783, 2021. Interaction, bond formation or reaction between a dimethylamino group and an adjacent alkene or aldehyde group in aromatic systems controlled by remote molecular constraints. CrystEngComm. ISSN 1466-8033

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Abstract

Peri-peri interactions in naphthalene systems control the degree of bond formation between a peri-dimethylamino group and a polarised alkene or aldehyde group. Two peri-phenyl groups, which repel, induce closer N⋯C interactions or bond formation, while the ethylene link in the corresponding acenaphthene system has the opposite effect, and for the more electron-deficient alkenes lead to formation of a fused azepine ring initiated by the tert-amino effect. In related 1,8-fluorene derivatives N⋯C interactions occur for an aldehyde and a moderately polarised alkene, but fused azocines are formed when the alkene is more reactive.

Item Type: Journal article
Publication Title: CrystEngComm
Creators: Bristow, J.C., Cliff, S.V.A., Yang, S. and Wallis, J.D.
Publisher: Royal Society of Chemistry (RSC)
Date: 27 May 2021
ISSN: 1466-8033
Identifiers:
NumberType
10.1039/d1ce00377aDOI
1447505Other
Rights: © The Royal Society of Chemistry 2021. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Divisions: Schools > School of Science and Technology
Record created by: Laura Ward
Date Added: 22 Jun 2021 15:52
Last Modified: 22 Jun 2021 15:52
URI: http://irep.ntu.ac.uk/id/eprint/43152

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