ChemInform Abstract: Reaction of Sterically Congested Thiones with Benzyne. The First Isolation of a Thioaldehyde—Benzyne Adduct.
Abstract
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ChemInform Abstract
Sterically congested aromatic thioaldehyde (I) reacts with benzyne, in situ generated from iodonium compound (II), to give a 1:1 thioaldehyde—benzyne adduct (III), the structure of which is confirmed by spectroscopic means. A radical mechanism is proposed for this synthesis. In contrast, normal cycloaddition of sterically congested aliphatic thioketone (IV) with benzyne leads to the [2 + 2] cycloadduct (V), whereas reaction of sterically less hindered thiocamphor (VI) with benzyne precursor (VII) leads to ene-reaction product (VIII).
