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A study on the Kabachnik-Fields reaction of benzaldehyde, cyclohexylamine, and dialkyl phosphites

journal contribution
posted on 2012-01-05, 00:00 authored by G Keglevich, N Z Kiss, D K Menyhárd, A Fehérvári, I Csontos
The Kabachnik–Fields reaction of benzaldehyde, cyclohexylamine, and dimethyl phosphite carried out at 80°C in acetonitrile takes place via an imine (PhC[DOUBLE BOND]N[BOND]cHex) intermediate, as the monitoring by in situ Fourier transform IR spectroscopy suggested. The corresponding α-hydroxyphosphonate was also formed in a quantity of 13% that was not converted to α-aminophosphonate under the conditions applied. The outcome was similar to the Kabachnik–Fields reaction with diethyl phosphite as the P-component. Molecular modeling and subsequent DFT calculations carried out under solventless conditions supported the experimental results and indicated the formation of a high number of ideally positioned H bonds as the key determinant for the conformation of the starting, intermediate, and product states. The relative energies of the possible intermediates were in accord with the observation that the formation of the α-hydroxyphosphonate is a “dead-end” route.

History

Journal

Heteroatom Chemistry

Volume

23

Issue

2

Pagination

171 - 178

Publisher

John Wiley & Sons

Location

Hoboken, N.J.

ISSN

1042-7163

eISSN

1098-1071

Language

eng

Publication classification

C1.1 Refereed article in a scholarly journal

Copyright notice

2011, Wiley Periodicals