An improved route to 1,2,4-trioxanes using tin(IV) as a hydrogen equivalent

Abstract

Bloodworth's route to the 1,2,4-trioxanes has been duplicated using tin(IV) as a hydrogen equivalent throughout. Thus a tetraallyltin compound is treated with singlet oxygen to give a tetraallylperoxytin compound; this adds to an aldehyde to give the tin derivative of a peroxyhemiacetal, and this tin alkoxide undergoes ring-closing intramolecular addition to the olefinic group in the presence of mercury (II) acetate to give the 1,2,4-trioxane.