Journal article
Organic synthesis in the solid state via hydrogen-bond-driven self-assembly
Journal of organic chemistry, Vol.73(9), pp.3311-3317
05/02/2008
DOI: 10.1021/jo8001563
PMID: 18370419
Abstract
This Perspective describes how chemists can control intermolecular [2 + 2] photodimerizations in the solid state using small molecules as linear templates. The templates assemble olefins into positions for the reaction via hydrogen-bond-driven self-assembly. We attach functional groups to the olefins that complement hydrogen bond donor and acceptor groups of the templates. The resulting cyclobutane-based products form stereospecifically, quantitatively, and in gram amounts. The templates are used to direct the formation of a [2.2]paracyclophane and ladderanes. The organic solid state is an exciting medium within which to control chemical reactivity since it is possible to synthesize, or construct, molecules that may be, otherwise, unobtainable from solution. The products form with a high degree of stereocontrol provided by a crystal lattice. The critical covalent-bond-forming process also occurs in a solvent-free environment. That molecules are virtually frozen in position in a solid also means that this methodology enables chemists to employ principles of molecular recognition and self-assembly to direct and conduct organic synthesis.
Details
- Title: Subtitle
- Organic synthesis in the solid state via hydrogen-bond-driven self-assembly
- Creators
- Leonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City 52242, USA
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.73(9), pp.3311-3317
- DOI
- 10.1021/jo8001563
- PMID
- 18370419
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 05/02/2008
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216564702771
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