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C=CbondspositionedviafourO-H∙∙∙Nhydrogenbondsfora[2+2]
photodimerization(Fig.7.1).Moreover,UVirradiationofthesolid
resulted in the stereocontrolled formation of 4,4
-tpcb in 100%
yield [18]. Res was separated from the cyclobutane product via basic
extraction [19].
Figure 7.1
X-ray structures of 2(4,4
-bpe)∙2(res)and(4,4
-tpcb)∙2(res)
co-crystals.
Following our initial work, we turned to expand the approach
by developing additional templates. In particular, we focused on a
naphthalene as a template in the form of 1,8-naphthalenedicarboxylic
acid(1,8-nap)(Fig.7.2)[20].Inparticular,co-crystallizationof1,8-
nap with 4,4
-bpewasshowntoproducethefiniteassembly2(1,8-
nap)·2(4,4
-
bpeviatwoO-H∙∙∙Nhydrogenbonds(Fig.7.2a).TheC=Cbondswere
organizedparallelandseparatedby3.73Å.UVirradiationproduced
4,4
-bpe). Each acid interacted with two molecules of 4,4
-tpcb in quantitative yield.
Figure 7.2
X-ray structures: (a) 2(1,8-nap)·2(4,4
-bpe), (b) 2(2,3-
nap)·2(fum), and (c) 2(Reb-im)·2(4,4
-bpe).
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