Disproportionation of p-nitrotoluene and p-nitroethylbenzene catalyzed by hydroxide ion in water by the action of β-cyclodextrin

ORGN 482

Yun Lu, yulu@siue.edu1, Zahra Khedra1, and Bo Liu2. (1) Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, (2) School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, China
p-Nitrotoluene and p-nitroethylbenzene were treated with aqueous solution of NaOH containing b-cyclodextrin (b-CD) at 65°C. Corresponding bibenzyl derivatives were produced. The disproportionation reaction proceeds by a benzylic carbanion intermediate produced from the deprotonation of the substrates by HO-, whose Bronsted basicity is believed to be enhanced in the special microenvironment in water created by CD. This work provides a method of green chemistry and assymmetric synthesis of bibenzyl derivatives.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007