ChemInform Abstract: Mono‐ and Dioxetanes of 2,5‐Anhydroalditols, Syntheses and Reactions.

Abstract

293ChemInform Abstract The tosylates (Ib) (from (Ia)), (Ic), or (Id) give the mono oxetanes (IIa), (IIb), or (IIc) on treatment with Na-methylate; use of an excess of methylate produces the dioxetane (III) exclusively. With some modifications, the compounds (IV), (Va), (Vb), and (VI) (from (Vb)) are similarly prepared. The treatment of the tosylate (VII) with Na methylate, however, leads to the dianhydro L-arabinitol (VIII). A series of reactions of the mono-and dioxetanes prepared are described. Thus, for instance, the compounds (IXa), (IXb), or (X) are obtained by reaction of HCl with (IIc), (III), or (IV), respectively. In the presence of MeOH, the methoxy compound (XI) is formed from (IIc). The reduction product (XII) is obtained from (III). Further, a synthesis of the "double-headed" muscarin relative (XIV) with ido configuration can be accomplished.