Synthesis of Partially Bridged Phosphonate and Thiophosphonate Resorcinarenes

Synthesis of new resorcinarene-based molecular clips

“…If only two equivalents of aryl reagents is used mostly the trans bis-substituted isomers are formed with high amount of trisubstituted and tetra-substituted products. However possible way was found using procedure published by Dalcanale´s group 4 . Partial hydrolysis of tetraphosphonate of resorcinarene led to high amount of cis bis-substituted isomer.…”

“…Our current research on methods for the synthesis of cavitands of reduced symmetry has now provided a new avenue to prepare resorcin [4]arene-based molecular clips and cis A 2 B 2 deeper cavitand.…”

“…Synthesis of resorcinarene cavitand is based mostly on two main sequential steps -preparation of resorcin [4]arene and bridging of phenols with (het)aryls (e.g. 1,2-difluro-4,5-dinitrobenzene -DFDNB).…”

Molecular Recognition with Ditopic Cavitand Re Complexes

“…The starting resorcinarene 14 [19] was bridged with 4-(α,α-dibromo-p-tolyl)pyridine to give the cavitand 3 in 31 % yield by a published procedure. [20] Treatment of 3 with Re-(CO) 5 Br (0.5 equiv.)…”

“…The AC-dithiophosphonate resorcinarene isomers 12a and 12b (Scheme 2) were obtained in good yields by the protocol reported in the literature. [19] The final bridging reactions were performed by addition of an excess of 4-(α,α-dibromotolyl)pyridine [1e] to DMF solutions of resorcinarene 12a or 12b in the presence of K 2 CO 3 (Scheme 2). The reactions led to the formation of both the out-out and the in-out isomers of 13a and 13b in 2.4:1 molar ratios.…”