Synthesis and dethreading reaction of a rotaxane-like complex of an octaoxa[22]ferrocenophane with dialkylammonium

Abstract

An octaoxa[22]ferrocenophane 1 composed of 1,1′-ferrocenylene and C6H4-1,2-{(OCH2CH2)3O}2 groups was employed as macrocyclic component of a rotaxane-like complex with dialkylammonium. Ru-catalysed cross-metathesis reaction of [{C6H3-3,5-(OMe)2}CH2NH2CH2C6H4-4-OCH2CH2CH = CH2]BARF (BARF = B{C6H3-3,5-(CF3)2}4) with CH2 = CHCOO(C6H4-4-C(C6H4-4-tBu)3) in the presence of 1 yielded rotaxane-like complex [(1){(C6H3-3,5-(OMe)2)CH2NH2CH2C6H4-4-OCH2CH2CH = CHCOO(C6H4-4-C(C6H4-4-tBu)3)}]BARF. It kept the interlocked structure in CDCl3, benzene-d 6 and toluene-d 8. Dissolution of the rotaxane-like complex in polar solvents, such as CD3CN and DMSO-d 6, caused the dethreading reaction to form the component molecules. A rotaxane having dibenzo[24]crown-8 as the macrocyclic component did not undergo the dethreading reaction in the solution.