Cycloaddition to an anthracene-derived macrocyclic receptor with supramolecular control of regioselectivity.
N-Ethylmaleimide and maleic anhydride add to the interior face of one anthracene wall with unusual 1,4-regioselectivity, whereas singlet oxygen adds to both anthracene walls with 9,10-regioselectivity.
Gassensmith
Jeremiah J
JJ
Department of Chemistry and Biochemistry, University of Notre Dame, IN 46556, USA.
Baumes
Jeffrey M
JM
Eberhard
Jens
J
Smith
Bradley D
BD
D000873:Anthracenes / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D005033:Ethylmaleimide / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008299:Maleic Anhydrides / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000873:Anthracenes; D047028:Macrocyclic Compounds; D008299:Maleic Anhydrides; D026082:Singlet Oxygen; C034020:anthracene; D005033:Ethylmaleimide