Author :
Mallakpour, shadpour E.,Butler, george B
Title of Article :
Ene reaction of (S)-(-)-4-(a-Methylbenzyl)-1,2,4-triazoline-3,5-dione with propylene. X-ray diffraction analysis of a single crystal of the brominated adduct
Title Of Periodical :
AMERICAN CHEMICAL SOCIETY MACROMOLCULES
Descriptors :
Ene reaction,X-ray diffraction,ouptically active triazoline diones,Model compound
Abstract :
Optically pure(S)-(-)-4-(a-methylbenzyl)-1,2,4-triazoline-3,5-dione was synthesized and its ene reaction with propylene carried out in order to obtain a model compound for further study in the modification of polydienes. The product was brominated to demonstrate that the absolute configuration of the dione had een retained and to study the N-H hydrogen bonding. The compounds were fully characterized by using H NMR. C NMR, and mass spectroscopy. A structural analysis of (S)-(-)-4-(r-methylbenzyl)-1-(2,3-dibromopropyl) urazole was performed via single-crystal X-ray diffraction. It crystallizes in space group P2***12***12***1 with four molecules in a unit cell of the following dimensions: a=5.985(2) A,b = 10.758 (3) A,c =23.063 (3) A,and V = 1484.8 (6) A**3. The sturucture was solved by the heavy-atom method and refined by least-squares techniques to give a final R = 0.066. The dihedral angle between the phenyl ring and the five-membered ring is 65.8, and oxygen is joined by the hydrogen bond to the N-H group [N(4)-H(4)-0(1)].
