Standard values of vicinal coupling constants in the assignment of relative configurations and conformational analysis of acyclic chiral carbinols and hydrocarbons

✍ Scribed by C. Alvarez Ibarra; M. T. Garcia Romo; M. S. Arias Perez

• Publisher: John Wiley and Sons
• Year: 1982
• Tongue: English
• Weight: 424 KB
• Volume: 18
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1270180411

✦ Synopsis

Abstract

Standard values of vicinal coupling constants are proposed in order to assign relative configuratations and analyse the conformational distribution of acyclic chiral carbinols and hydrocarbons. Thus, the assignment of relative configurations has been achieved for the diastereomeric carbinols, (2__R__4__R__, 2__S__4__S__)‐ and (2__R__4__S__, 2__S__4__R__)‐5,5‐dimethyl‐4‐phenyl‐2‐hexanol and (1__R__3__R__, 1__S__3__S__)‐ and (1__R__3__S__, 1__S__3__R__)‐1‐mesityl‐4,4‐dimethyl‐3‐phenyl‐1‐pentanol, through the analysis of the respective vicinal coupling constants and the corresponding conformational distribution. The analysis of the vicinal coupling constants allows the establishment of the monoconformational character of the (2__R__4__S__, 2__S__4__R__) diastereomer in the first case and the (1__R__3__R__, 1__S__3__S__) diastereomer in the second case.