A chiral crown ether 1 was synthesized from (R)-1,1′-bi-2-naphthol. Chiral rotaxanes were prepared by end-capping of pseudorotaxanes consisting of 1 and secondary ammonium salts. An ammonium salt bearing terminal anthracene group gave stable pseudorotaxane. Chiral induction was observed during end-capping by radical conjugate addition of a bulky thiol to the pseudorotaxane bearing methacrylate group at the terminus.
Selective O-acylation of aminoalcohols by a bulky acid anhydride in the presence of trifluoromethanesulfonic acid and dibenzo-24-crown-8 afforded [2]rotaxane in high yields. An acid halide could be used as an acylating reagent in the presence of silver trifluoromethanesulfonate.
Treatment of (η3-allyl)bromopalladium complexes with tricarbonylnitrosyl ferrate [Fe(CO)3(NO)]−1 afforded (η3-allyl)dicarbonylnitrosyliron complexes in good yields. The reaction provides a new route to (η3-allyl)dicarbonylnitrosyliron complexes by transmetallation of the η3-allyl ligand from palladium to iron metal.
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