19985-34-3Relevant academic research and scientific papers
Kinetic Study of Substituent Effects on the Mechanism of β-Elimination of Arenethiol from trans-2,3-Bis-(arylthio)-4-nitro-2,3-dihydrothiophenes in Toluene
Petrillo, Giovanni,Novi, Marino,Garbarino, Giacomo,Dell'Erba, Carlo
, p. 1741 - 1746 (1985)
The 2,3-dihydrothiophene derivatives (1b-f) readily undergo, in toluene, regiospecific tributylamine-promoted syn-elimination of arenethiol to give the 2-(arylthio)-4-nitrothiophenes (2b-f).For the rather complex kinetic behaviour displayed by each member of the series, a rationalisation is proposed based on a stability of the substrate's conjugate base sufficient to allow formation of non-negligible concentrations of an intermediate ion pair along the reaction co-ordinate.The system allows direct conclusions to be drawn concerning the leaving-group expulsion step: an advanced extent of bond cleavage between carbon and the leaving group can be postulated in the transition state.
