Premium
Structure of the products of condensation of hydroxylamine with trifluoromethyl‐β‐diketones: assignments of the diastereotopic protons of the 4‐methylene group in 5‐hydroxy‐5‐trifluoromethyl‐Δ 2 ‐isoxazolines
Author(s) -
Sanz Dionisia,
Claramunt Rosa M.,
Singh Shiv P.,
Kumar Vinod,
Aggarwal Ranjana,
Elguero José,
Alkorta Ibon
Publication year - 2005
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.1676
Subject(s) - chemistry , trifluoromethyl , methylene , hydroxylamine , coupling constant , nuclear magnetic resonance spectroscopy , condensation , chemical shift , medicinal chemistry , proton nmr , stereochemistry , computational chemistry , organic chemistry , alkyl , physics , particle physics , thermodynamics
Abstract The combined use of 1 H NMR spectroscopy with theoretical calculations of chemical shifts (GIAO) and coupling constants (B3LYP/6‐311 ++G**) of a 5‐hydroxy‐5‐trifluoromethyl‐Δ 2 ‐isoxazoline has enabled solving the problem of the assignments of the diastereotopic protons in this compound. This result has been extended to 5‐hydroxy‐5‐trifluoromethyl‐Δ 2 ‐pyrazolines and the corresponding 5‐trichloromethyl derivatives. Copyright © 2005 John Wiley & Sons, Ltd.