The Mills-Nixon effect. IV. Base-catalysed cleavage of Trimethylsilyl-veratrol, -1,3-benzodioxole and -1,4-benzodioxan derivatives

Abstract

The rates of cleavage for 4-trimethylsilyl-veratrol, 5-trimethylsilyl-1,3-benzodioxole and 6-trimethyl- silyl-1,4-benzodioxan have been measured at 30ºC in 1 : 9 water-dimethyl sulphoxide containing sodium hydroxide. The benzodioxole derivative is more reactive than the other two substrates; this enhanced reactivity arises from hybridization changes enforced on the ring junction carbons by the strained dioxole ring.