Optical Rotatory Dispersion Studies. 137. Synthesis and Chiroptical Properties of α- and β-Deuterium Substituted Aliphatic Aldehydes and Ketones

Article abstract of DOI:10.1021/jo00183a007

The synthesis and chiroptical properties of (2R)-2-deuterio-3-hexanone (8a), (2R)-2-deuterio-4-methylpentanone (8b), (2R)-2-deuteriopentanal (9a), (2R)-2-deuterio-3-methylbutanal (9b), and (3R)-3-deuteriohexanal (13) are described.All exhibit Cotton effects consistent with the preferred eclipsed conformation of the carbonyl/α-alkyl moiety.The β-deuterio aldehyde 13 shows a sign change in accordance with the "proximity rule" previously observed in CD studies.