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Issue 3, 2016
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Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis

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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.

Graphical abstract: Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis

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Article information


Submitted
15 Nov 2015
Accepted
15 Dec 2015
First published
22 Dec 2015

Org. Chem. Front., 2016,3, 319-323
Article type
Research Article

Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis

L. Yang, L. Song, C. Huang, M. Huang and B. Liu, Org. Chem. Front., 2016, 3, 319
DOI: 10.1039/C5QO00373C

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