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Optical Rotatory Dispersion Studies. 137. Synthesis and Chiroptical Properties of α- and β-Deuterium Substituted Aliphatic Aldehydes and Ketones
Gorthey, Lee Ann,Vairamani, Mariappanadar,Djerassi, Carl
, p. 1511 - 1517 (1984)
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.
