Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis
Literature Information
Publication Date
2015-12-22
DOI
10.1039/C5QO00373C
Impact Factor
5.281
Authors
Li Yang, Liqiang Song, Chong Huang, Mingzheng Huang, Bo Liu
View Original
Abstract
The synthesis of strained paracyclophanes is challenging and generally delivers low yields. A novel strategy of installing an ortho-substituent group to the ethereal oxygen is developed to facilitate the formation of oxygen-containing [10]paracyclophane via RCM macrocyclization. By rationally modulating the electronic and steric effects in the single and double ortho-substitution modes, efficient RCM macrocyclization was achieved for different substrates to form the corresponding [10]paracyclophane products, in which all newly generated double bonds were in the E-form. The development of this methodology will enrich the chemistry of ring-closing metathesis related to the formation of strained macrocycles.
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Source Journal
Organic Chemistry Frontiers
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7.8
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8.7%
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724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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