Jump to main content
Jump to site search

Issue 38, 2012
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
14 May 2012
Accepted
11 Jul 2012
First published
13 Jul 2012

Org. Biomol. Chem., 2012,10, 7763-7779
Article type
Paper

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

A. Lari, M. B. Pitak, S. J. Coles, G. J. Rees, S. P. Day, M. E. Smith, J. V. Hanna and J. D. Wallis, Org. Biomol. Chem., 2012, 10, 7763
DOI: 10.1039/C2OB25929J

Social activity

Search articles by author

Spotlight

Advertisements