A plausible reaction mechanism of the intra- and intermolecular nucleophilic substitutions to prompt transetherification.

<p>A plausible reaction mechanism of the intra- and intermolecular nucleophilic substitutions to prompt transetherification.</p

Ether formation between 1 and 2.

<p>Ether formation between 1 and 2.</p

Ether formation between tetraethylene glycol tosylate 2a and a) monoalcohol 8, b) propane-1,3-diol 11 and c) 2-(hydroxymethyl)propane-1,3-diol 13.

<p>Reaction time was 12 h. Yields were calculated based on the isolated amounts. ND: not detected.</p

MALDI-TOF-MS spectrum of the crude product extracted by CHCl₃ for the reaction in Table 1, Entry 1.

<p>Structures of 6 and 7 are shown in <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0091912#pone-0091912-g003" target="_blank">Figure 3</a>. Matrix: α-cyano-4-hydroxycinnamic acid.</p