Stereoselective Photochemical Reaction of Cyclohexyl Phenyl Ketone within Lytropic Liquid Crystals Formed by Chiral Ionic Liquids | Zendy

Yang Xiujie | Zendy; Li Xinwei | Zendy; Chen Bin | Zendy; Wu Lizhu | Zendy; Zhang Liping | Zendy; Zheng Liqiang | Zendy; Tung Chenho | Zendy

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Stereoselective Photochemical Reaction of Cyclohexyl Phenyl Ketone within Lytropic Liquid Crystals Formed by Chiral Ionic Liquids

Author(s) -

Yang Xiujie,

Li Xinwei,

Chen Bin,

Wu Lizhu,

Zhang Liping,

Zheng Liqiang,

Tung Chenho

Publication year - 2013

Publication title -

chinese journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.28

H-Index - 41

eISSN - 1614-7065

pISSN - 1001-604X

DOI - 10.1002/cjoc.201300275

Subject(s) - chemistry , bromide , stereoselectivity , ionic liquid , ketone , enantiomer , enantioselective synthesis , racemization , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis

Irradiation of cyclohexyl phenyl ketone ( 1 ) results in either intra‐ or intermolecular hydrogen abstraction to afford compounds 1‐phenylhept‐6‐en‐1‐one ( 2 ) and α ‐cyclohexyl benzyl alcohol ( 3 ) as photoproducts, in which 3 has a pair of enantiomers. Herein, two types of chiral hexagonal liquid crystals were prepared to direct the enantioselective photochemical reaction of 1 . One of the hexagonal liquid crystals is composed of 1‐tetradecyl‐3‐methylimidazolium bromide/ p ‐xylene/H 2 O with the modification by a chiral inductor. The other one is formed by chiral ( S )‐3‐hexadecyl‐1‐(1‐hydroxy‐propan‐2‐yl)‐imidazolium bromide/ p ‐xylene/H 2 O. The product analysis shows that the latter one can be used as a microreactor to achieve stereoselective photochemical reaction, while the former one produced compound 3 with no enantioselectivity at all.

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