1,2,3-Dithiazolyl and 1,2,35-Dithiadiazolyl Radicals as Spin-Bearing ...

often generated in situ although was also isolated prior to the subsequent addition of the
methylating agent. This addition usually resulted in no colour change indicative of
substitution. Aliquots taken at several intervals revealed by 1 H NMR that the unchanged
anion was still present. If left for 16 hours or more these solutions would often take on a
red colour which was found to be due to the starting material III-1 being reformed as
confirmed by NMR. Several attempts were also made to substitute a benzyl group on the
oxygen atom using benzyl bromide to obtain III-5, however these attempts were met with
similar results to those seen in the reactions targeting III-4. It is believed that the salts
formed from alkali metal containing bases tended not to react based on the strong
interaction of the ions in solution which prevented the necessary close approach of the
alkylating agent of choice.
III-4 Meerwein’s Salt III-5
3.5 Conclusions and Future Work
The attempts made to alkylate III-1 are far from exhaustive and so it is possible that
a route can be uncovered which will provide isolation of compounds III-4 and III-5.
These compounds could open up the door to the formation of coordination complexes of
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