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 and Pitak, Matuesz B. and Coles, Simon J. and Rees, Gregory J. and Day, Stephen P. and Smith, Mark E. and 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 and Biomolecular Chemistry, 10 (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
Journal or Publication Title:
Organic and Biomolecular Chemistry
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
Departments:
ID Code:
65009
Deposited By:
Deposited On:
06 Jun 2013 09:07
Refereed?:
Yes
Published?:
Published
Last Modified:
01 Jan 2020 08:31