Ba. Trofimov et al., Reaction of pyrrole anions with carbon disulfide. Synthesis of pyrrole-3-carbodithioates, TETRAHEDRON, 56(37), 2000, pp. 7325-7329
2,5-Disubstituted pyrroles react with carbon disulfide in the system KOH-DM
SO with selective formation of pyrrole-3-carbodithioate anions from which p
yrrole-3-carbodithioates were prepared by ethylation in 36-61% yield. From
2-methyl-5-phenyl(2-furyl- or 2-thienyl)pyrroles only pyrrole-3-carbodithio
ates are formed, wi th no isomeric pyrrole-4-carbodithioates being present.
The reaction direction depends on pyrrole ring substitution: unsubstituted
pyrrole selectively forms pyrrole-1-carbodithioate, whereas 2-methyl-, 2,3
- and 2,4-dimethylpyrroles give exclusively pyrrole-2-carbodithioates under
the same conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.