Repozytorium

Diastereoselective synthesis of tetraalkyl (R,R)-1,2-cyclohexylene-diamino-di-phosphonates bearing thiophene, furan and pyrrole moieties. Computational and experimental study on their formation.

Autorzy

Anna Chrostowska

Clovis Darrigan

Said Khayar

Patric Baylère

Jarosław Lewkowski

Anna Krzyczmonik

Paweł Tokarz

Katarzyna Ślepokura

Tadeusz Lis

Rok wydania

2015

Czasopismo

Tetrahedron

Numer woluminu

71

Strony

2561-2571

DOI

10.1016/j.tet.2015.03.010

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

Diastereoselective additions of dialkyl phosphites to three diimines bearing DACH moiety and thiophene, furan or pyrrole rings were studied in the aspect of their stereochemistry, structure of predominant products and mechanism. For these reasons, analysis of reaction mixture, X-ray studies of products, UV-photoelectron spectroscopy and ionization energies of the starting imines were performed experimentally while reaction profiles were calculated at the CAM-B3LYP/6-311G(d,p) level of theory. The calculated energy barriers corresponding to the gas phase are significantly low and seem to explain why the products are formed relatively easily.

Słowa kluczowe

diamino-phosphonate with DACH moiety, diastereoselective addition of phosphite, X-ray structural study, UV-photoelectron spectroscopy, ionization energies, quantum calculation

Adres publiczny

http://dx.doi.org/10.1016/j.tet.2015.03.010

Strona internetowa wydawcy

http://www.elsevier.com

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