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Friscić T, Drab DM, MacGillivray LR. A test for homology: photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols. Org Lett. 2004;6(25):4647-50doi: 10.1021/ol0484052.
Friscić, T., Drab, D. M., & MacGillivray, L. R. (2004). A test for homology: photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols. Organic letters, 6(25), 4647-50. https://doi.org/10.1021/ol0484052
Friscić, Tomislav, et al. "A test for homology: photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols." Organic letters vol. 6,25 (2004): 4647-50. doi: https://doi.org/10.1021/ol0484052
Friscić T, Drab DM, MacGillivray LR. A test for homology: photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols. Org Lett. 2004 Dec 09;6(25):4647-50. doi: 10.1021/ol0484052. PMID: 15575651.
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Org Lett. 2004 Dec 09;6(25):4647-50. doi: 10.1021/ol0484052.

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

Organic letters

Tomislav Friscić, David M Drab, Leonard R MacGillivray

Affiliations

  1. Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.

PMID: 15575651 DOI: 10.1021/ol0484052

Abstract

[reaction: see text] 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.

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