Tris(1,3-dihydroxy-2-propyl)amine, a planar trialkylamine: Synthesis, structure, and properties

ORGN 575

Peter Livant, livanpd@auburn.edu1, Yuanping Jie, jieyuan@auburn.edu1, Minmin Yang, yangmin@auburn.edu1, Hui Li, lihui@mail.utexas.edu2, Wei Zhu, zhuwei1@auburn.edu1, Vince Cammarata, cammavi@auburn.edu1, Yu Qin1, Eric Bakker3, Tyler A. Sullens, sullety@auburn.edu1, and Philip M. Almond1. (1) Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849, (2) Chemistry Department, University of Texas, Austin, TX, (3) Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907
The title compound (1) was synthesized in five steps from dihydroxyacetone dimer. The key step was an insertion of a Rh-carbenoid into the N-H bond of bis(2,2-dimethyl-1,3-dioxan-5-yl)amine, which proceeded in over 80% yield. The x-ray structure of 1 revealed a virtually planar nitrogen (sum of C-N-C angles = 359.05(7)°; T = 193 K, R = 3.61%,). The pKa of 1 indicated it is an unusually weak base; the x-ray structure of 1·HCl was determined. Cyclic voltammetry of 1 showed a one-electron oxidation process which was, notably, reversible.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005