Efficient Stereo- and Regiocontrolled Alkene Photodimerization through Hydrogen Bond Enforced Preorganization in the Solid State

Feldman, Ken S.; Campbell, Robert F.

doi:10.1021/jo00112a007

Cited by 79 publications

(58 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Owing to the modularity of the approach, we reasoned that it should be possible to engineer molecules that possess structures largely preorganized, 13 in a similar way to resorcinol, to align olefins within discrete assemblies, giving rise to template libraries. 8 Here, we reveal the ability of 14 would juxtapose two bipyridines in the solid for [2 + 2] photoreaction. To our knowledge, 1,8-nap represents the second example of a molecule that functions as a linear template by controlling reactivity within a discrete hydrogen-bonded molecular assembly in the solid-state.…”

mentioning

confidence: 83%

Exploiting modularity in template-controlled synthesis: a new linear template to direct reactivity within discrete hydrogen-bonded molecular assemblies in the solid state

2001

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 83%

Exploiting modularity in template-controlled synthesis: a new linear template to direct reactivity within discrete hydrogen-bonded molecular assemblies in the solid state

2001

View full text Add to dashboard Cite

show abstract

“…Feldman and Campbell [95] demonstrated that a 'J'-shaped naphthoic acid-derived cinnamic acid 59 could assemble to a dimer in the solid state through carboxylic acid synthons, where the HT alignments of two olefins conform to the topochemical criteria Fig. 3.30 a The structures of three aromatic dicarboxylates.…”

Section: Self-complementary Reactantsmentioning

confidence: 99%

Hydrogen Bonding in Supramolecular Crystal Engineering

Wang

Zheng

2015

Lecture Notes in Chemistry

View full text Add to dashboard Cite

This chapter emphases the important role of hydrogen bonding in crystal engineering for preparing fascinating architectures and engineering desired properties. The relatively high directionality and strength of hydrogen bonds make the prediction and control of molecular orientation in organic solids practical and reliable. Especially, strong hydrogen bonds like O-H···O, O-H···N, and N-H···O interactions are more useful. The introduction of supramolecular synthons and retrosynthesis theory has helped crystal chemists a lot in understanding and designing more complex structures. A large number of crystal structures reported in Cambridge Structure Database (CSD) provided a helpful tool for searching and analyzing specific interaction modes. Up to now, with the development of basic concepts and principles and the wide applications, the subject of crystal engineering has matured. Various intriguing structures and complicated entanglements have been constructed based on hydrogen bonds, such as nanocapsules, nanotubes, and n-Borromean arrayed topologies. The crystal engineering strategy has lent chemists the ability to control solid state reactions regio-and stereo-specifically and improve the physicochemical properties of drugs using pharmaceutical cocrystals. In addition, it will be seen that hydrogen bonding can also be used to prepare robust porous materials for gas adsorption and separation.

show abstract

“…bonded systems are involved affords cyclobutanes with the α-truxillate structure 125 . A molecular dynamic study of the dimerization of 3-and 4-cyanocinnamic acids in a microcrystalline environment has been carried out 126 .…”

Section: A Cinnamic Acid and Its Derivativesmentioning

confidence: 99%

Photochemistry of Cyclobutanes: Synthesis and Reactivity

Horspool

2009

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

Introduction Cycloaddition Reactions Involving Alkenes Cycloaddition Reactions Involving Dienes and Trienes Cycloadditions of Enones and Related Compounds Photochemistry of Ketones Cage Compounds Cyclobutane Ring Opening Reactions

show abstract

Efficient Stereo- and Regiocontrolled Alkene Photodimerization through Hydrogen Bond Enforced Preorganization in the Solid State

Cited by 79 publications

References 0 publications

Exploiting modularity in template-controlled synthesis: a new linear template to direct reactivity within discrete hydrogen-bonded molecular assemblies in the solid state

Exploiting modularity in template-controlled synthesis: a new linear template to direct reactivity within discrete hydrogen-bonded molecular assemblies in the solid state

Hydrogen Bonding in Supramolecular Crystal Engineering

Photochemistry of Cyclobutanes: Synthesis and Reactivity

Contact Info

Product

Resources

About