Book chapter
Chapter 10 Hydrogen-bond-mediated organic synthesis in the solid state
Strategies and Tactics in Organic Synthesis, pp.368-382
2008
DOI: 10.1016/S1874-6004(08)80014-7
Abstract
This chapter illustrates that small organic molecules, in the form of linear templates, can be used to direct the [2 + 2] photodimerization in the solid state. The ability to achieve independent control of solidstate reactivity by exploiting the process of self-assembly is used to construct molecular targets, such as a [2.2]paracyclophane and [n]- ladderanes, in quantitative yield and gram amounts. The organic solid state represents an intriguing medium within which to control the formation of covalent bonds. The solid state is sufficiently flexible to allow atoms to move and react, yet sufficiently rigid to enable reactions to proceed with remarkable stereocontrol. The homogeneous nature of the solid state means that covalent-bond-forming reactions that occur can proceed in up to quantitative yield. The benefit of controlling the formation of covalent bonds in such a solvent-free environment is apparent. The solid state also enables molecules to adopt geometries impossible to achieve in the liquid phase. This means that opportunities exist to form molecules in the solid state that may be inaccessible in solution.
Details
- Title: Subtitle
- Chapter 10 Hydrogen-bond-mediated organic synthesis in the solid state
- Creators
- Leonard R MacGillivray - Department of Chemistry University of Iowa Iowa City, IA 52242, USA
- Resource Type
- Book chapter
- Publication Details
- Strategies and Tactics in Organic Synthesis, pp.368-382
- DOI
- 10.1016/S1874-6004(08)80014-7
- ISSN
- 1874-6004
- Language
- English
- Date published
- 2008
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216582902771
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