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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.