We hypothesized that both diol and ketone organomercurial products were the result of a series of reactions, cascading in one-pot (Scheme 8A). Our previous work with the formation of 6-membered cyclic silanediol organomercurials and their ring opening using either 1M HCl in THF or NaBH4 in DMF laid the foundation for our continued mechanistic investigations. We have previously established 6-membered organomercurial compounds such as 65 are facilely opened in the presence of acid to form rearranged allylic silanol compounds such as 66. Diastereoselective, 5-exo-ring closure would form silanediol 67. Intramolecular attack by the pendant mercury species would form transient mercuronium 68; elimination would form silyl enol ether 69, which could collapse into ketone product 70.