Addition of dimethyl phosphite to N,N'-dialkyl- and -diaryl terephthalaldimines and its stereochemistry contrary to behavior of other analogues

Autor:	Maria Rodriguez-Moya, Jarosław Lewkowski, Anna Ignaczak, Justyna Obiedzińska, Rafał Karpowicz
Rok vydání:	2016
Předmět:	Inorganic Chemistry 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Organic chemistry Dimethyl phosphite 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 191:751-758
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426507.2015.1091825
Popis:	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 behaviour of these reactions was studied by NMR demonstrating, that the reactions lead to the formation of both possible diastereomeric forms in 1:1 up 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::70fc521750f948c092b909e387a3909e https://doi.org/10.1080/10426507.2015.1091825 Zobrazit plný text záznamu