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. 2010 Nov;58(11):1517-20.
doi: 10.1248/cpb.58.1517.

New formation mechanism of allylic trithiocarbonates from sodium O-(2-Alkenyl) dithiocarbonates via sequential pericyclic reactions: Density functional theory study

Masashi Eto  1 , Koki Yamaguchi, Yasuyuki Yoshitake, Kazunobu Harano
Affiliations
Free article

New formation mechanism of allylic trithiocarbonates from sodium O-(2-Alkenyl) dithiocarbonates via sequential pericyclic reactions: Density functional theory study

Masashi Eto et al. Chem Pharm Bull (Tokyo). 2010 Nov.
Free article

Abstract

Density functional theory (DFT) calculations at the B3LYP/6-31G(d) level demonstrated that sodium O-(3-phenylallyl) dithiocarbonate undergoes [3,3]-sigmatropic rearrangement to sodium S-(1-phenylallyl) dithiocarbonate, which then isomerizes to the more thermodynamically stable sodium S-(3-phenylallyl) dithiocarbonate. The calculations also showed that sodium 2-alkenyl trithiocarbonates and their esters are more labile towards the allylic rearrangement.

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