Tosylates s. p-Toluenesulfonic

Here, we consider electropolymerized 3,4-ethylenedioxythiophene (EDT), prepared with different supporting electrolytes (see [135]) polystyrenesulfonic add (PSS), p-toluenesulfonic acid (Tos), and tetrabutylammonium perchlorate (BU4NCIO4). The anion produced from the dissociation of toluene-sulfonic acid is also called tosylate (< -SO i). Additionally, we address chemically prepared PEDOT-PSS, in a water emulsion, sodium free (<0.5 ppm), provided by Agfa Gevaert N.V. None of these blends contains PSS -Na" ", as was the case for Baytron P discussed above. The conductivity values a obtained for the polymers are summarized in Table 21.1. PEDOT/Tos is the most conductive (450 S cm ). The polyanion-based materials give lower conductivities 80 S cm for electropolymerized PEDOT-PSS and 0.03 S cm for chemically polymerized PEDOT-PSS. 

The phase transfer cyanide reaction appears to be superior even to the reaction conducted in dipolar aprotic media. 5-Chlorooctane, for example, yields 85—90% substitution products and only 10—15% elimination products under phase transfer conditions [1], whereas the homogeneous reaction in dimethyl sulfoxide resulted in only 70% of s-cyanooctane [8]. The phase transfer reaction is applicable for chloride, bromide, or methanesulfonate leaving groups but is less satisfactory when the nucleo-fuge is either iodide or p-toluenesulfonate (tosylate). This is due to the fact that the large, lipophilic and polarizable quaternary cations tend to ion pair irreversibly with iodide and tosylate. This difficulty can often be overcome by renewing the aqueous reservoir of nucleophile. 

An ale. soln. of 2-acetyl-l,3-indandione added dropwise during 0.5-1 hr. to a refluxing soln. of 1,8-naphthalenediamine and p-toluenesulfonic acid monohydrate in anhydrous ethanol, and refluxed an additional 24hrs. 2-methylperimidine via its tosylate. Y 72%. F. e. s. W. A. Mosher and T. E. Banks, J. Org. Chem. 36,1477 (1971). 

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