SYNTHESIS OF FORMYL DERIVATIVES OF BENZOCROWN ETHERS CONTAINING N, S,AND O HETEROATOMS IN THE MACROCYCLE

A method for the synthesis of 4'-bromobenzodithia-15(18)-crown-5(6) an d 4'-bromobenzodiaza-15(1 8)-crown-5(6) by condensation of 3,4-di(2'-h aloethoxy)bromobenzene with polyoxaalkanes containing terminal SH or N HMe groups was suggested. The method for the synthesis of formyl deriv atives of benzocrowns containing N, S, and O heteroatoms in the macroc ycle based on the metallation of appropriate bromo derivatives with Bu (n)Li followed by treatment of the resulting organolithium intermediat es with DMF was developed. Oximes and semicarbazones of benzaldehydes containing a crown ether fragment were obtained, and their transformat ion into the original aldehydes by treatment with KNO2 in an acid medi um was studied.