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Structural elucidation of dioxa‐cage compounds from tetrahydroisobenzofuran‐1(3 H )‐one: analysis of NMR data and GIAO chemical shifts calculations
Author(s) -
Resende Gabriela,
Alvarenga Elson Santiago
Publication year - 2016
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4483
Subject(s) - chemistry , chemical shift , undecane , computational chemistry , carbon 13 nmr , atomic orbital , density functional theory , cage , halogenation , stereochemistry , organic chemistry , physics , mathematics , quantum mechanics , combinatorics , electron
The polycyclic compounds, especially the dioxa‐cages, have attracted considerable attention in recent years. In our work, a series of 9 β ‐substituted 3‐oxo‐4,11‐dioxatetracyclo[5.2.1.1 5,8 .0 2,6 ]undecane compounds were unexpectedly isolated during bromination, chlorination and epoxidation reactions of the 3‐hydroxy‐3a,4,7,7a‐tetrahydro‐4,7‐methanoisobenzofuran‐1(3 H )‐one. After careful analysis of the NMR data, the chemical shifts of the isolated and the expected products were predicted by theoretical calculations using density functional theory and gauge including atomic orbitals. The best correlation between calculated and experimental data was evaluated by comparing mean absolute errors and applying DP4 probability methodology. Results from both approaches indicated a correct structural elucidation. Copyright © 2016 John Wiley & Sons, Ltd.