The ammonia-free partial reduction of substituted pyridinium salts was written by Donohoe, Timothy J.;Johnson, Dale J.;Mace, Laura H.;Thomas, Rhian E.;Chiu, Jessica Y. K.;Rodrigues, Jason S.;Compton, Richard G.;Banks, Craig E.;Tomcik, Peter;Bamford, Mark J.;Ichihara, Osamu. And the article was included in Organic & Biomolecular Chemistry in 2006.Formula: C4H8ClI This article mentions the following:
This paper reports a study into the partial reduction of N-(alkyl)pyridinium salts together with subsequent elaboration of the intermediates thus produced. Activation of a pyridinium salt by placing an ester group at C-2, allows the addition of two electrons to give a synthetically versatile enolate intermediate which can be trapped with a variety of electrophiles. Furthermore, the presence of a 4-methoxy substituent on the pyridine nucleus enhances the stability of the enolate reaction products, and hydrolysis in situ gives stable dihydropyridone derivatives in good yields. These versatile compounds are prepared in just three steps from picolinic acid and can be derivatized at any position on the ring, including nitrogen when a p-methoxybenzyl group is used as the N-activating group on the pyridinium salt. This publication describes an exploration of the optimum reducing conditions, the most appropriate N-alkyl protecting group, as well as the best position on the ring for the methoxy group. Electrochem. techniques which mimic the synthetic reducing conditions are utilized and they give clear support for a proposed mechanism of reduction in which there is a stepwise addition of two electrons to the heterocycle, mediated by di-tert-butylbiphenyl. Moreover, there is a correlation between the viability of reduction of a given heterocycle under synthetic conditions and its electrochem. response; this offers the potential for use of electrochem. in predicting the outcome of such reactions. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Formula: C4H8ClI).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Formula: C4H8ClI
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com