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Paper | Regular issue | Vol 60, No. 5, 2003, pp.1123-1132
Published online, 17th March, 2003
DOI: 10.3987/COM-03-9714
Equilibrium between Bis(1,3-oxazolidin-3-yl)methanes and 3,8-Dioxa-1,6-diazabicyclo[4.4.1]undecanes

Raúl Salas-Coronado, Juan Carlos Gálvez-Ruiz, Carlos Guadarrama-Pérez, and Angelina Flores-Parra*

*Department of Chemistry, Centro de Investigación y de Estudios Avanzados del I.P.N., A.P. 14-740, C.P. 07000 México, D.F., Mexico, D.F.

Abstract

The equilibrium between bis(1,3-oxazolidin-3-yl])methanes (A) and 3,8-dioxa-1,6-diazabicyclo[4.4.1]undecanes (B) is reported. A and B were prepared from formaldehyde and (±)-1-methylethanolamine (1), 2,2-dimethyl-ethanolamine (2), (1S, 2R)-1-methyl-2-phenylethanolamine (3), ethanolamine (4), (R)-2-carboxyethanolamine methyl ester (5), (S)-2-ethylethanolamine (6), (R)-2-phenylethanolamine (7). The equilibrium depends on the substituents. Thermodynamic structures (A) derived from 5 and 7 by slow crystallization are completely transformed into undecanes (B) by an equilibrium asymmetric transformation. Structures were established by 1H, COSY, HETCOR and NOESY NMR experiments. Preferred conformer of the undecane ring was identified.