V. S. Babaitsev

Sigmatropic rearrangements of alkenyl benzofuryl and benzothienyl sulfides

The thio Claisen rearrangement of 2-butenyl 2-benzofuryl sulfide, cyclopenten-2-yl 2-benzofuryl sulfide, 2-butenyl 2-benzothienyl sulfide, and cyclopenten-2-yl 2-benzothienyl sulfide was investigated. The rates, energies and entropies of activation of the process were calculated, and the effect of the structure of the sulfide, the polarity of the solvent, and the temperature was demonstrated by comparison of these values. The 1,3-thioallyl rearrangement of 1-methylallyl 3-methyl-2-benzothienyl sulfide was studied, and it was shown that this reaction competes with the thio Claisen rearrangement.

Electronic absorption spectra and acidities of heteroaromatic thiols

The electronic absorption spectra of a number of substituted and unsubstituted thiophene-, benzothiophene-, and benzofuranthiols were studied, and their ionization constants were determined by establishment of the dependence of the optical densities of aqueous alcohol solutions of them on the pH.