Peroxides of Sterically Hindered Derivatives of Schlenk Hydrocarbon Diradical

1997 ◽  
Vol 62 (19) ◽  
pp. 6524-6528 ◽  
Author(s):  
Andrzej Rajca ◽  
Suchada Rajca ◽  
Shailesh R. Desai ◽  
Victor W. Day
Keyword(s):  
Sterically Hindered ◽  
Derivatives Of

Bis(ether) derivatives of tetrakis(2-hydroxyphenyl)ethene — Direct synthesis of (E)- and (Z)-bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene via the McMurry olefination reaction

2006 ◽  
Vol 84 (10) ◽  
pp. 1250-1253 ◽  
Author(s):  
Mee-Kyung Chung ◽  
Paul Fancy ◽  
Jeffrey M Stryker
Keyword(s):  
Supramolecular Chemistry ◽  
Direct Synthesis ◽  
Protecting Groups ◽  
Tert Butyl ◽  
Orthogonal Protection ◽  
Protection Strategies ◽  
Titanium Trichloride ◽  
Sterically Hindered ◽  
Derivatives Of

The direct synthesis of sterically hindered, partially etherified derivatives of tetrakis(2-hydroxyphenyl)ethene is reported by using the McMurry reductive olefination reaction on a range of differentially substituted 2,2′-dialkoxy benzophenone substrates. Three orthogonal protection strategies are demonstrated, incorporating β-silylethyl, 3-butenyl, and tert-butyl protecting groups, respectively, into the starting benzophenones. The latter proved most efficient, with both the McMurry coupling and deprotection steps occurring concomitantly under the McMurry conditions to directly yield the desired bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene as a 1:1 mixture of E- and Z-diastereoisomers.Key words: preorganized polyaryloxide ligands, McMurry olefination, titanium trichloride, supramolecular chemistry, tetrakis(2-hydroxyphenyl)ethene, 2,2′-disubstituted benzophenone.

Sign in / Sign up

Export Citation Format

Share Document