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Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde

Record type: Article

The X-ray crystal structures of salts and zwitterionic Knoevenagel products from 1-dimethylamino-naphthalene-8-carbaldehyde show long N-C bonds between peri-groups which provide models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes respectively. For the salts the N-C bonds lie in the range 1.625-1.638 angstrom with C-OH bonds intermediate in length between single and double bonds, while for the zwitterions the N-C bonds lie in the range 1.612-1.660 angstrom. The structural assignment of the former is supported by solid state C-13 and N-15 NMR studies on doubly isotopically-labelled material. Several zwitterions were converted to naphtha[1,8-bc]azepines by a mechanism involving the tertiary amino effect.

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Citation

Lari, A, Pitak, Mateusz, Coles, Simon J., Rees, Gethin, Day, S.P., Smith, M.E., Hanna, J.V. and Wallis, J.D. (2012) Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde Organic & Biomolecular Chemistry, 10, (38), pp. 7763-7779. (doi:10.1039/C2OB25929J).

More information

Published date: 2012
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 345863
URI: http://eprints.soton.ac.uk/id/eprint/345863
ISSN: 1477-0520
PURE UUID: 1767d560-d014-4050-8f36-0b4d1b13ddb0
ORCID for Mateusz Pitak: ORCID iD orcid.org/0000-0002-3680-7100
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 04 Dec 2012 17:35
Last modified: 18 Jul 2017 05:07

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Contributors

Author: A Lari
Author: Mateusz Pitak ORCID iD
Author: Simon J. Coles ORCID iD
Author: Gethin Rees
Author: S.P. Day
Author: M.E. Smith
Author: J.V. Hanna
Author: J.D. Wallis

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