A test for homology: Photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols

被引:53
作者
Friscic, T [1 ]
Drab, DM [1 ]
MacGillivray, LR [1 ]
机构
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
关键词
D O I
10.1021/ol0484052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cocrystallization of trans-1,2-bis(4-pyridyl)ethylene (4,4'-bpe) with eight members of a homologous series of phloroglucinols 1a-h yields molecular solids 2(1a-h)-2(4,4'-bpe) with components held together by four O-H...N hydrogen bonds. In each case, the molecules assemble to form a discrete four-component assembly with olefins preorganized for a [2 + 2] photodimerization. UV irradiation of each member in the series of solids produces rctt-tetrakis(4-pyridyl)cyclobutane (4,4'-tpcb), stereospecifically, in up to 100% yield.
引用
收藏
页码:4647 / 4650
页数:4
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