34736-69-1Relevant articles and documents
The Reaction of Diols with Triphenylphosphine and Di-isopropyl Azodicarboxylate. Part 1. Formation of Cyclic Phosphoranes from 1,3- and 1,4-Diols
von Itzstein, Mark,Jenkins, Ian D.
, p. 437 - 446 (2007/10/02)
Triphenylphosphine and di-isopropyl azodicarboxylate react with propane-1,3-diol and butane-1,4-diol in tetrahydrofuran at 0 deg C to give cyclic dioxytriphenylphosphoranes that appear to be oligomeric.Under conditions of high-dilution, however, the expected six- and seven-membered-ring phosphoranes are formed.Contrary to a previous report, propane-1,3-diol does not undergo cyclodehydration to give oxetane, but gives instead a pyrazolidine derivative, Substituted, and conformationally restricted, 1,3- and 1,4-diols form the expected six- and seven-membered-ring cyclic phosphoranes without recourse to high-dilution techniques.A 13C n.m.r. method for disthinguishing apical from equatorial phenyl groups in phosphoranes is reported: dialkoxytriphenylphosphoranes bearing an apical phenyl group exhibit much smaller one-bond coupling constants (1JP-C 120 Hz) than those containing only equatorial phenyl groups (1JP-C > 170 Hz).
