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 1477-0520

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Abstract

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
ISSN:	1477-0520
Date:	2012
Volume:	Vol.10
Number:	No.38
Page Range:	pp. 7763-7779
Identification Number:	10.1039/c2ob25929j
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
URI:	http://wrap.warwick.ac.uk/id/eprint/50840

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