PMR and IR spectra of a new class of macrocyclic compounds

Synthesis of Phosphorus-Containing Macrocycles and Cryptands

“…94 Phospho dihydrazides (CeH50)P(S)(NHNH2)2 react with dichlorohexamethyltrisiloxane to give mixtures of eight-, nine-, and 10-membered rings 66a-c (Scheme Analogous reactions are undertaken starting directly from polyethylene glycols or related species which are reacted with dior trihalogenated phosphorus compounds in the presence of base: derivatives of type 67 and compounds 68a,c are thus prepared (Table 6). [109][110][111][112][113][114][115][116] Extension of this method allows the synthesis of macrocycles 70,117-118 71,119 72,120 73,121 74,122-124 75,125 and 76116'126'127 (Chart 1). The reaction of P-functionalized macrocycles 67b and 76 with amines allows the preparation of other macrocyclic species.115 '127 The macrobicyclic derivative 77 is formed in 46% yield by cyclizing o-NaOCe^CKC^C^OlnCeKUONa-o (n = 2, 3) with adamantanediphosphonic dichloride.116 '128 When p-fer£-butylcalix[6]arene 78 is treated with cesium fluoride and then with ethyl phosphorodichloridite, an ethyl phosphate substituent is introduced onto the lower rim of the calix [6]arene.…”