Synthesis and Stereochemical Properties of “Extended” Biphenols Bridged by ortho-, meta-, and para-Phenylene Spacers
✍ Scribed by Mariusz M. Gruza; Jean-Claude Chambron; Enrique Espinosa; Emmanuel Aubert
- Book ID
- 102828930
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 601 KB
- Volume
- 2009
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
A series of isomeric biphenols based on para-(1), meta-(2), and ortho-(3) terphenyl backbones was synthesized. Suzuki cross-coupling methodology was employed for the construction of the terphenyl backbone of their methyl-protected precursors (respectively 8, 13, and 16). Using K 2 CO 3 as the base, the best reaction conditions involved DMF at 100 °C as solvent. Anhydrous conditions greatly improved the yields of the sterically crowded systems (particularly 16). ortho-Terphenyls 3 and 16 exist as mixtures of syn/anti atropisomers in solution. Compound 16 crystallizes in the anti-in form. DFT