Helvetica Chimica Acta – Vol. 89 (2006)
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polar effects in these reactions are unimportant [34]. We are confident that the kinetics
data reported in this work will find wide and general use in mechanistic and synthetic
applications. For example, the effect of b-hydroxy substituents and the concept of
enhancing reactivity through H-bonding are worth of further consideration in aqueous
solution.
I would like to thank Mr. Marco Ballestri for his valuable technical assistance and Dr. Carla Ferreri
for helpful discussions.
Experimental Part
Toluene or benzene, containing a small amount of nonane, decane, or undecane as internal GC
standards, were used as solvent. Samples containing ca. 0.5M of (TMS)3SiH, the appropriate thiol, and
G
bromide 1 (or selenide 8), with a thiol/substrate ratio of ꢃ20 :1, were degassed in Wheaton reactors.
Reactions were initiated with the aid of AIBN (=2,2’-azobis(isobutyronitrile)) at 808. The products of
interest were identified by comparison of their retention times with those of authentic materials.
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