Stereochemical study of iminodihydrofurans based on experimental measurements and SOPPA calculations of (13)C-(13)C spin-spin coupling constants.
Configurational assignment and conformational analysis of a series of iminodihydrofurans obtained from cyanoacetylenic alcohols were performed on the basis of experimental measurements and high-level ab initio calculations of their (13)C-(13)C spin-spin coupling constants. The title compounds were shown to form and exist in solution as the individual Z isomers, adopting the orthogonal orientation of the amino, alkylamino and dialkylamino groups and the s-trans orientation of the CONH(2) group at the C(4) position of the 2,5-dihydro-2-iminofuran moiety.
A. E. Favorsky Institute of Chemistry, Irkutsk, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia. krivdin_office@irioch.irk.ru
Leonid B
LB
Krivdin
Spartak S
SS
Khutsishvili
Olesya A
OA
Shemyakina
Anastasiya G
AG
Mal'kina
Boris A
BA
Trofimov
Rubén H
RH
Contreras
D000438:Alcohols / Q000737:chemistry; D000465:Algorithms; D005663:Furans / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation
D000438:Alcohols; D005663:Furans; D007097:Imines