Oxymercuration-demercuration of (±)-(1α,3α,3aβ,6aβ)- 1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol Dibenzoate

Abstract

Oxymercuration of (±)-(1α,3α,3aβ,6aβ)-1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol dibenzoate 1 was performed with mercuric tetrafluoroborate alone, in the presence of tetrafluoroboric acid and with tetrafluoroboric acid + sodium acetate and demercuration with sodium borohydride in 3N NaOH. The hydration of the alkene was selective toward the symmetric alcohol at short time, but at prolonged time, the symmetric and un-symmetric alcohols were obtained in a near 1:1 ratio. Anyway, the oxymercurationdemercuration of alkene 1 is a slow hydration reaction.