13544-04-2Relevant articles and documents
A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic
Baumann, Marcus,Baxendale, Ian R.,Deplante, Fabien
, p. 2549 - 2560 (2017)
An assembled suite of flow-based transformations have been used to rapidly scale-up the production of a novel auxin mimic-based herbicide which was required for preliminary field trials. The overall synthetic approach and optimisation studies are describe
Efficient methods for the synthesis of arylacetonitriles
Stazi, Federica,Maton, William,Castoldi, Damiano,Westerduin, Pieter,Curcuruto, Ornella,Bacchi, Sergio
experimental part, p. 3332 - 3338 (2010/11/20)
Various approaches to [2-fluoro-4-(trifluoromethyl)phenyl]acetonitrile were investigated. Two of these methods were selected and applied to a variety of electron-deficient substrates, thereby expanding the scopes of the procedures.
Kinetics of proton transfer from 2-nitro-4-X-phenylacetonitriles to piperidine and morpholine in aqueous Me2SO. Solvent and substituent effects on intrinsic rate constants. Transition state imbalances
Bernasconi, Claude F.,Wenzel, Philip J.
, p. 11446 - 11453 (2007/10/03)
Rate constants (k1(B)) for the deprotonation of 2-nitro-4-X-phenylacetonitrile, 2-X (X = NO2, SO2CH3, CN, CF3, Br, and Cl) by piperidine and morpholine and for the reverse reaction (k-1(BH)) have been determined in 90% Me2SO- 10% water, 50% Me2SO-50% water, and water (X = NO2, SO2CH3, CN only). Bronsted β(B) values (dlog k1(B)/dpK(a)(BH)), Bronsted α(CH) values (dlog k1(B)/dlog K(a)(CH)), and intrinsic rate constants (log k(o) = log(k1/q) for pK(a)(BH)-p K(a)(CH) + log(p/q) = 0) were calculated from these data. α(CH) is smaller than β(B), implying an imbalance wnich is consistent with a transition state in which delocalization of the negative charge into the 2-nitrophenyl moiety lags behind proton transfer. A consequence of this imbalance is that the intrinsic rate constant decreases with increasing electron withdrawing strength of X. For π-acceptor substituents (NO2, SO2CH3, CN) there is a further decrease in k(o) due to a lag in the delocalization of the charge into X. The intrinsic rate constants depend very little on the Me2SO content of the solvent which is shown to be the result of compensation of mainly two competing factors. One is the stabilization of the polarizable transition state by the polarizable Me2SO which increases k(o); the other is attributed to a lag in the solvation of the developing carbanion behind proton transfer at the transition state which leads to a decrease in k(o).
