Reactions of cyrene with formaldehyde

Cyrene reacts with 35% aqueous formaldehyde in the presence of K₂CO₃, tetramethylguanidine and Et₃N to give three products, viz., major α,α-bis(hydroxymethyl) derivative, a product of its keto group reduction, and 3,5,11,12-tetraoxatricyclo[7.2.1.0^2,7]dodecan-2-ol. The options for the derivatization of the hydroxy groups with benzyl, tosyl, isopropylidene, and methylene acetal protecting groups were studied.