Self-assembling bisurea macrocycles used as an organic zeolite for a highly stereoselective photodimerization of 2-cyclohexenone.
We report a highly selective 2 + 2 cycloaddition of 2-cyclohexenone in the presence of self-assembled bisurea macrocycles that yields the head-to-tail photodimer. The reaction proceeds with high conversion and with decreased incidence of secondary photorearrangement. Furthermore, the product can be extracted from the assembly, and the solid assembly is readily recovered and reused, much like a zeolite.
Yang
Jun
J
Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA.
Dewal
Mahender B
MB
Shimizu
Linda S
LS
D002625:Chemistry, Organic; D003512:Cyclohexanones / Q000737:chemistry*; D019281:Dimerization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D010777:Photochemistry; D016062:Porosity; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry*; D017641:Zeolites / Q000737:chemistry*
D003512:Cyclohexanones; D047028:Macrocyclic Compounds; D017641:Zeolites; C028215:2-cyclohexen-1-one; D014508:Urea