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

Lari, A, Pitak, MB, Coles, SJ, Rees, GJ, Day, SP, Smith, ME, Hanna, JV and Wallis, JD ORCID: 0000-0001-7259-8783, 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. ISSN 1477-0539

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Abstract

The X-ray crystal structures of salts and zwitterionic Knoevenagel products from 1-dimethylaminonaphthalene-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 Å 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 Å. The structural assignment of the former is supported by solid state 13C and 15N 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.

Item Type: Journal article
Publication Title: Organic & Biomolecular Chemistry
Creators: Lari, A., Pitak, M.B., Coles, S.J., Rees, G.J., Day, S.P., Smith, M.E., Hanna, J.V. and Wallis, J.D.
Publisher: Royal Society of Chemistry
Date: 2012
Volume: 10
Number: 38
ISSN: 1477-0539
Identifiers:
NumberType
10.1039/C2OB25929JDOI
Rights: © Royal Society of Chemistry 2012
Divisions: Schools > School of Science and Technology
Depositing User: EPrints Services
Date Added: 09 Oct 2015 09:44
Last Modified: 09 Jun 2017 13:09
URI: http://irep.ntu.ac.uk/id/eprint/1869

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