Rearrangement reactions have been a topic of interest to the synthetic community for more than a century, but only recently have they become a line of investigation in our laboratory. In general, rearrangements can be demarcated into two categories. One contains true pericyclic processes, which are concerted and proceed through cyclic transition states ; such reactions often require vigorous heating or the addition of Lewis acid additives. Another class of rearrangement reactions is comprised of those that proceed through discrete organometallic intermediates. Our laboratory recently disclosed the first rearrangement reaction of primary allylic silanols into secondary ones (Scheme 1). Strictly speaking, this reaction was a formal rearrangement and required a two-step, two-pot protocol. First, primary allylic silanols were transformed into 6-membered silanediol organomercurial heterocycles using a combination of Hg(OTf)2 and NaHCO3. Following purification by silica-gel chromatography, treatment of these heterocycles with 1M aqueous HCl in THF or with NaBH4 in DMF allowed for demercurative cleavage into secondary silanol products bearing terminal alkenes.