Journal of the Chemical Society. Perkin transactions II p. 1741 - 1746 (1985)
Update date:2022-09-26
Topics:
Petrillo, Giovanni
Novi, Marino
Garbarino, Giacomo
Dell'Erba, Carlo
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.
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