Synthesis and Reactions of 1,3,4,6-Tetra-2-thienylthienothiophene

Article abstract of DOI:10.1021/jo00001a018

1,3,4,6-Tetra-2-thienylthieno<3.4-c>thiophene (1f) was synthesized from di-2-thenoylmethane after five steps.The cycloaddition reaction of 1f with N-phenylmaleimide yielded a pair of exo (major) and endo (minor) adducts 7 and 8, whose structures were assigned on the basis of the difference in the reactivity toward m-chloroperbenzoic acid.The reaction of 1f with phenyl vinyl sulfoxide, dimethyl acetylenedicarboxylate, and di-2-thenoylacetylene gave benzothiophene derivatives 13, 15, and 16, respectively.