Addition of dimethyl phosphite to N,N'-dialkyl- and -diaryl terephthalaldimines and its stereochemistry contrary to behavior of other analogues |
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| Authors: | Jarosław Lewkowski Anna Ignaczak Rafał Karpowicz Justyna Obiedzińska Maria Rodriguez-Moya |
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| Institution: | 1. Department of Organic Chemistry, Faculty of Chemistry, University of ?ód?, ?ód?, Polandjlewkow@uni.lodz.pl;3. Department of Theoretical and Structural Chemistry, Faculty of Chemistry, University of ?ód?, ?ód?, Poland;4. Department of Organic Chemistry, Faculty of Chemistry, University of ?ód?, ?ód?, Poland |
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| Abstract: | The addition of dimethyl phosphite to N,N'-terephthalylidene-alkyl- (or aryl-) amines resulted in new tetramethyl 1,4-phenylene-bis-(N-alkylaminomethyl)-phosphonates in moderate yields. The stereochemical behavior of these reactions was studied by NMR, demonstrating that the reactions lead to the formation of both possible diastereomeric forms from 1:1 to 1:2 ratios. This was unexpected considering that previously investigated additions of diethyl, dibenzyl, and diphenyl phosphites to terephthalaldimines were diastereoselective up to 100%. Attempts were made to find reasonable explanation for the phenomenon using semi-empirical and DFT calculations. |
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| Keywords: | Diaminophosphonates terephthalic moiety stereochemistry dimethyl phosphite |
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