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1 H and 13 C NMR spectral data for a tricyclic derivative of a Diels–Alder adduct
Author(s) -
Pedersoli Susimaire,
Constantino Mauricio Gomes,
José da Silva Gil Valdo
Publication year - 2006
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.1714
Subject(s) - chemistry , adduct , homonuclear molecule , nmr spectra database , carbon 13 nmr , computational chemistry , resonance (particle physics) , derivative (finance) , diels–alder reaction , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , spectral line , molecule , financial economics , economics , physics , particle physics , astronomy , catalysis
Abstract A complete NMR analysis with full assignment for 1 H and 13 C NMR spectral data for 5‐(acetyloxy)‐3‐hydroxy‐9,10‐dimethoxy‐6‐oxo‐11‐oxatricyclo[6.2.1.0 2,7 ]undec‐2‐yl acetate (8) is described. This compound was prepared by rapid hydrogenation of the unstable Diels–Alder adduct obtained from the reaction between 3,4‐dimethoxyfuran (4) and 2,5‐diacetoxy‐1,4‐benzoquinone (5). Full homonuclear hydrogen coupling constants measurements and molecular mechanics calculations were performed for the determination of the relative stereochemistry. Copyright © 2005 John Wiley & Sons, Ltd.