Abstract
Abstract Diethoxytriphenylphosphorane. DTPP. prepared by reaction of triphenylphosphine and diethyl peroxide. is a “hydrolytically active” dioxyphosphorane which promotes mild and efficient cyclodehydration of diols to cyclic ethers in neutral media. Simple 1,2-, 1,4-, and 1,5-diols afford good yields of the cyclic ethers but 1,3-propanediol and 1,6-hexanediol give mainly 3-ethoxy-1-propanol and 6-ethoxy-1-hexanol. respectively. with DTPP. Tri- and tetra-substituted 1,2-diols afford the relatively stable 1,3,2-dinxaphospholanes in the presence of DTPP and the reaction conditions dictate whether epoxides, ketones, or allylic alcohols are obtained.
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