Photodimerization of 2-Naphthalenecarbonitrile inγ-Cyclodextrin Aqueous Solution

doi:10.7517/j.issn.1674-0475.2008.06.433

Abstract

Abstract: The development of highly selective and efficient photochemical reactions is one of the fundamental challenges in organic synthesis.Our recent studies reveal that irradiation of 2-naph-thalenecarbonitrile in organic solution with a light λ>280 nm results in the formation of three rigid cubane-like photodirners,anti-head-to-head 1,anti-head-to-tail 2 and syn-head-to-tail 3.In the present work,γ-cyclodextrin was used to direct the photodimerization of 2-naphthalenecarbonitrile. The results demonstrate that in the presence of γ-CD,the photodimerization takes place efficiently and regioselectively.The anti-head-to-head dimer 1 was obtained as the main product,while no products were detected by HPLC in host-free aqueous solution.

Key words: γ-cyclodextrin, 2-naphthalenecarbonitrile, photodimerization, regioselectivity

CLC Number:

LIAO Gui-hong, TONG Zhen-he(TUNG Chen-ho), WU Li-zhu. Photodimerization of 2-Naphthalenecarbonitrile inγ-Cyclodextrin Aqueous Solution[J]. Imaging Science and Photochemistry, 2008, 26(6): 433-437.

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