56437-47-9Relevant academic research and scientific papers
One-pot synthesis of sulfonyl (E)-stilbenes by nitrobenzene-mediated dimerizative desulfonation of benzylic sulfones
Chang, Meng-Yang,Chen, Yi-Chia,Lin, Shin-Ying,Chan, Chieh-Kai
, p. 1740 - 1747 (2014/03/21)
A facile one-pot synthetic route for preparing sulfonyl (E)-stilbenes 4 is developed. The efficient route is realized by a nitrobenzene (PhNO 2)-mediated dimerizative desulfonation of benzylic sulfones 3 in the presence of sodium hydride (NaH) in good yields. Some synthetic investigations of sulfonyl stilbenes 4 are also examined.
REACTIONS OF β-HALOSULPHONES WITH BASES AND SILVER SALTS: THE SULPHONYL GROUP AS A WEAK ANCHIMERIC ASSISTANT
Carretero, J.C.,Ruano, J.L. Garcia,Martinez, M.C.,Rodriguez, J.H.
, p. 4417 - 4423 (2007/10/02)
In order to obtain evidence about the ability of the sulphone group as anchimeric assistant, the behaviour of the erythro and threo-1,2-dimethyl (and 1,2-diphenyl)-2-halo-1-methylsulphonylethanes in their reactions with NH4OH/CH3CN, NaOH/MeOH and AgBF4/MeOH is described.The participation is not detected in any case on butane derivates or on 1,2-diphenylethane derivatives with basic nucleophiles, which yielded mainly elimination products.Reactions of the last compounds with AgBF4/MeOH only afforded mixtures of substitution products, with predominance of those with the same configuration of the starting sulphones in the case of erythro-derivatives, which must only evolve through an SN1 mechanism in competition with the anchimeric assistant process.This is the first reported result suggesting that the weak nucleophilic character of the sulphonylic oxygens can determine its participation as anchimeric assistant in the substitution of good leaving groups in β-position.
