A methodology for the determination of the stereoselectivity in the addition of thiols to indene is described. The chemical method employs an S-deuterio thiol, the thermal elimination reaction of the sulfoxides derived from the adducts, and the determination of the D content in the resulting indene. The preferred spectroscopic method employs 1,1,3-trideuterioindene and the LIS technique in the NMR analysis of the sulfones derived from the thiol-olefin adduct. The methodology employed is illustrated with a set of addition reactions carried out at room temperature under photochemically induced conditions and employing equimolar mixtures of 1,1,3trideuterioindene and a series of substituted thiophenols. Under these conditions the relative amount of cis adduct increased proportionally with the constants of the substituents.
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