Decarboxylation Facilitated by Carbocation Formation and Rearrangement during Steam Distillation of Vetiver Oil.
Density functional theory (DFT) calculations are used to probe the validity of mechanistic proposals for the conversion of isozizanoic acid to 12-norisoziza-5-ene, a reaction that occurs during steam distillation of vetiver oil. While this conversion corresponds overall to a simple decarboxylation, a multistep mechanism involving carbocation intermediates is supported by the computational results.
Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
Henry B
HB
Wedler
Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
T
T
Newman
Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
Dean J
DJ
Tantillo
D049930:Chrysopogon / Q000737:chemistry*; D003653:Decarboxylation; D057168:Distillation; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D009822:Oils, Volatile; D010938:Plant Oils / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D013227:Steam
D009822:Oils, Volatile; D010938:Plant Oils; D013227:Steam