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Prof. Yoshida explains, "We developed a method for synthesizing stable o-bromobenzenethiol equivalents by bromothiolation of aryne intermediates with an appropriate hydrogen sulfide equivalent and an electrophilic brominating reagent, resulting in controlled reactivity at the sulfur atom which prevents subsequent additions with aryne intermediates."

The researchers utilized potassium xanthate instead of hydrogen sulfide, owing to its better reactivity in aryne reactions and pentafluorophenyl bromide as an electrophilic brominating reagent.

He showed that the two types of ion are both intermediates in electrophilic reactions, but in different ways.

A similar partitioning of ortho/para versus meta pathways is well known in synthetic chemistry, and is widely exploited in electrophilic aromatic substitution reactions.

G.D.S. thanks E. Sorensen for explaining electrophilic aromatic substitution reactions.