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Orthoamides and Iminium Salts, LXXV (1). Contribution to the Formation of 2-Formyl-1,1,3,3-tetramethylguanidine and the Isomeric 1,1-Dimethyl-3-dimethylaminomethylene-urea

Orthoamides and Iminium Salts, LXXV (1). Contribution to the Formation of... 2-Formyl-1,1,3,3-tetramethylguanidine (1) could be prepared from tris(dimethylamino)ethoxymethane (3a) and formamide (4). Surprisingly, guanidine 1 does not result from the reaction of 1,1,3,3-tetramethylguanidine with formylating reagents such as dimethylamino-methoxy-acetonitrile (8) or the N,N-dimethylformamide-dimethylsulfate adduct (9), rather the isomeric 1,1-dimethyl-3- dimethylaminomethylene-urea (2) is formed. The structure of 2 was confirmed by NMR spectroscopy and crystal structure analysis. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Orthoamides and Iminium Salts, LXXV (1). Contribution to the Formation of 2-Formyl-1,1,3,3-tetramethylguanidine and the Isomeric 1,1-Dimethyl-3-dimethylaminomethylene-urea

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References (4)

Publisher
de Gruyter
Copyright
Copyright © 2012 by the
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2012-0406
Publisher site
See Article on Publisher Site

Abstract

2-Formyl-1,1,3,3-tetramethylguanidine (1) could be prepared from tris(dimethylamino)ethoxymethane (3a) and formamide (4). Surprisingly, guanidine 1 does not result from the reaction of 1,1,3,3-tetramethylguanidine with formylating reagents such as dimethylamino-methoxy-acetonitrile (8) or the N,N-dimethylformamide-dimethylsulfate adduct (9), rather the isomeric 1,1-dimethyl-3- dimethylaminomethylene-urea (2) is formed. The structure of 2 was confirmed by NMR spectroscopy and crystal structure analysis.

Journal

Zeitschrift für Naturforschung B – de Gruyter

Published: Apr 1, 2012

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