Issue 1, 2014

Regiospecific photodimerization reactions of an unsymmetrical alkene in two coordination compounds

Abstract

Two coordination complexes [Cd2(CBA)4(4-spy)4] (1) and [Cd2(5-NO2-1,3-BDC)2(5-NO2-1,3-HBDC)2(H2O)4]·(4-spy–H)2 (2) were prepared by the hydrothermal reactions of Cd(NO3)2·4H2O, 4-styrylpyridine (4-spy) and 4-chlorobenzoic acid (HCBA) or 5-nitrobenzene-1,3-dicarboxylic acid (5-NO2-1,3-H2BDC). Each pair of 4-spy molecules in [Cd2(CBA)4(4-spy)4] and [Cd2(5-NO2-1,3-BDC)2(5-NO2-1,3-HBDC)2(H2O)4]·(4-spy–H)2 are arranged in a head-to-head (HH) or head-to-tail (HT) fashion, which, upon UV irradiation, dimerizes into 1,2-bis(4-pyridyl)-3,4-bis(phenyl)cyclobutane (HH-ppcb) or 1,3-bis(4-pyridyl)-2,4-bis(phenyl)cyclobutane (HT-ppcb) in 100% yield, respectively. Compared with liquid-phase organic reactions, these solid-state photochemical [2 + 2] cycloadditions of olefin molecules provide good opportunities to synthesize regiospecific cyclobutanes.

Graphical abstract: Regiospecific photodimerization reactions of an unsymmetrical alkene in two coordination compounds

Supplementary files

Article information

Article type
Paper
Submitted
13 Aug 2013
Accepted
12 Sep 2013
First published
13 Sep 2013

CrystEngComm, 2014,16, 76-81

Regiospecific photodimerization reactions of an unsymmetrical alkene in two coordination compounds

D. Liu and J. Lang, CrystEngComm, 2014, 16, 76 DOI: 10.1039/C3CE41609G

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