Chiral Resolution of Intramolecular Cubane-Like Photodimers from Alkyl bis-2-Naphthoates

doi:10.7517/j.issn.1674-0475.2012.05.321

Abstract

Abstract: The photodimerization of polymethylene bis-2-naphthoates (N-M_n-N, n=2, 3, 4, 5) is very dependent on the length of alkyl chain in cyclohexane. Under light irradiation, N-M₃-N gave both anti-head-to-head and syn-head-to-head photodimers, while N-M₄-N and N-M₅-N each exclusively produced anti-head-to-head photodimer with high yield and high regioselectivity. Importantly, the intramolecular anti-head-to-head cubane-like photodimer has been successfully resolved into its enantiomers by HPLC.

Key words: polymethylene bis-2-naphthoates, intramolecular photodimerization, cubane-like photodimers, regioselectivity, chiral resolution

CLC Number:

CHENG Su-fang, CHEN Bin, ZHANG Li-ping, TONG Zhen-he(TUNG Chen-ho), WU Li-zhu. Chiral Resolution of Intramolecular Cubane-Like Photodimers from Alkyl bis-2-Naphthoates[J]. Imaging Science and Photochemistry, 2012, (5): 321-329.

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