The role of β-cyclodextrin in mediating regioselective dimethylaminomethylation of phenol. Issue 2 (11th January 2018)

• Record Type: Journal Article
• Authors: Wu, Wen-Hai; Duan, Jiang; Wei, Ting; Tu, Hai-Yang; Zhang, Ai-Dong
• Is Part Of: Tetrahedron. Volume 74:Issue 2(2018)
• Page Start: 360
• Page End: 365
• Publication Date: 2018-01-11
• Subjects: Supramolecular chemistry -- β-cyclodextrin -- Mannich reaction -- Regioselectivity -- Product-inclusion mechanism; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.12.007
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Regioselective reactions with supramolecular control are of great interest. Herein, the para -regioselectivity in the Mannich reaction of phenol with formaldehyde and dimethylamine was achieved with the use of β-cyclodextrin (β-CD), giving 4-( N, N -dimethylaminomethyl)phenol ( p -AP) as major product. 1 H NMR and ITC measurements of the binding of β-CD with the reactants and the products o - and p -AP revealed a new mechanism, in which β-CD includes p -AP instead of phenol to control the reaction regioselectivity. This product-inclusion mechanism is remarkably different to the known reactant-inclusion process. Graphical abstract: