Stereochemistry of the intermediates in the synthesis of 1,4,7,10-tetraazacyclododecane from triethylenetetramine, glyoxal and diethyl oxalate
Tetrahedron, ISSN: 0040-4020, Vol: 62, Issue: 29, Page: 6855-6861
2006
- 12Citations
- 12Captures
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Article Description
The equilibrium and rearrangement phenomena encountered in two steps for the synthesis of 1,4,7,10-tetraazacyclododecane from triethylenetetramine, glyoxal and diethyl oxalate were studied and elucidated after the development of two micellar electrokinetic chromatographic (MEKC) methods. The latter were able to separate: (i) the four bis-aminals ( 2 – 5 ) obtained from the condensation of triethylenetetramine with glyoxal; (ii) the four diones ( 6 – 9 ) derived from the reaction of the bis-aminals with diethyl oxalate, whose solid state structures were determined by single crystal X-ray diffraction. The three not yet reported diones ( 6, 7 and 9 ) were synthesised by taking advantage of both the reaction conditions and the use of a particular catalyst (MeONa). A plausible reaction mechanism, as well as a discussion of the solid state structures, is presented.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040402006007290; http://dx.doi.org/10.1016/j.tet.2006.04.099; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=33745024259&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040402006007290; https://api.elsevier.com/content/article/PII:S0040402006007290?httpAccept=text/xml; https://api.elsevier.com/content/article/PII:S0040402006007290?httpAccept=text/plain; https://dx.doi.org/10.1016/j.tet.2006.04.099
Elsevier BV
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