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Assignment of relative configurations and conformational study of acyclic diastereomeric ketones
Author(s) -
AlvarezIbarra C.,
AriasPérez M. S.,
Moya E.
Publication year - 1990
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.1260280711
Subject(s) - diastereomer , chemistry , geminal , vicinal , coupling constant , stereochemistry , chemical shift , computational chemistry , organic chemistry , physics , particle physics
Abstract The conformational analysis and the assignment of relative configurations [( RR , SS ) and ( RS , SR )] to the dia‐stereomeric racemates of two acyclic ketones with two asymmetric carbons, ±‐2,2,7,7‐tetramethyl‐5,6‐diphenyloctan‐3‐one and ±‐5,5‐dimethyl‐1,3,4‐triphenylhexan‐1‐one, have been achieved by analysis of 1 H‐ 1 H geminal and vicinal coupling constants, 13 C– 1 H direct coupling constants and 13 C chemical shifts. This study allows the establishment of the monoconformational character of the ( RR , SS ) diastereomers. The application of the empirical equation of Haasnoot et al. supports this hypothesis.