Synthesis of substituted 14-Crown-4 compounds

Seventeen new substituted 14-crown-4 derivatives 3-10, 35-40, 42, 45 and 46 are described. A series of nine compounds 2-10 with two, three or four substituents in the 6- and/or 13-positions was synthesized in good yields from the appropriate diols and ditosylates using improved cyclization conditions. The solid state structures of 6,6,13,13-tetra(benzyloxymethyl)-14-crown-4 (8) and lithium thiocyanate complexes of trans- and cis-6,13-bis(spiro-2,2-dichlorocyclopropyl)-14-crown-4 (45) and (46), respectively, have been determined.