The cathodic reduction of O-ethyl S-phenacyl dithiocarbonate (1) yields O-ethyl (benzoyl)-thioacetate (2) and O-ethyl S-[(ethoxythiocarbonyl)(phenacyl)]-dithiocarbonate (3) through an Eschenmoser process with an electrogenerated base (EGB).
References
1.
LundH., Acta Chem. Scand., (1960), 14, 1927.
2.
FuchigamiT., KandeeZ. E. S., and NonakaT., Bull. Chem. Soc. Jap., (1986), 59, 338.
LammB., and SamuelssonB., Acta Chem. Scand. (1969), 23, 691.
5.
HornerL., and SingerR. J., Chem. Ber., (1968), 101, 3329.
6.
SchwabeK., and VoigtJ., Z. Elektrochem., (1952), 56, 44.
7.
SimonetJ., Supplement S: The Chemistry of sulphur-containing functional groups, PataiS., and RappoportZ., (eds) John Wiley and Sons, Chichester, 1993, pp. 439.
8.
ChugaevL.A., Chem. Ber., (1899), 32, 3332.
9.
(a) DjerassiC., J. Am. Chem. Soc., (1955), 77, 568
10.
MoriK., and NakamuraY., J. Org. Chem., 1969, 34, 4170.
11.
(a) DelducP., TailhanC., and ZardS. Z., J. Chem. Soc. Chem. Commun., (1988), 308
12.
BartonD.H. R., ParekhS. I., and TseC., Tetrahedran Lett., (1993), 34, 2733
13.
CrichD., and QuinteroL., Chem. Rev., (1989), 89, 1413.
14.
BridgesA.J., and WhithamG. H., J.C.S. Perkin I, (1975), 1603.
