Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes : salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde
Lari, Alberth, Pitak, Matuesz B., Coles, Simon J., Rees, Gregory J., Day, Stephen P., Smith, Mark E., Hanna, John V. and Wallis, John 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, Vol.10 (No.38). pp. 7763-7779. ISSN 1477-0520Full text not available from this repository.
Official URL: http://dx.doi.org/10.1039/C2OB25929J
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 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|
|Divisions:||Faculty of Science > Physics|
|Journal or Publication Title:||Organic & Biomolecular Chemistry|
|Publisher:||Royal Society of Chemistry|
|Page Range:||pp. 7763-7779|
|Access rights to Published version:||Restricted or Subscription Access|
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