MoOPH

MoOPH
Names
Other names
Oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide)[1]
Vedejs Reagent
Identifiers
3D model (JSmol)
ChemSpider
  • InChI= 1S/C6H18N3OP.C5H5N.Mo.2O2.O/c1-7(2)11(10,8(3)4)9(5)6;1-2-4-6-5-3-1;;2*1-2;/h1-6H3;1-5H;;;;/q;;+4;2*-2;
    Key:  PPRBHGIGPWBROO-UHFFFAOYSA-N
  • c0cccc[n+]0[Mo-2]12(OO1)(OO2)(=O)[O+]=P(N(C)C)(N(C)C)N(C)C
Properties
C11H23MoN4O6P
Molar mass 434.25 g·mol−1
Appearance Yellow crystals[1]
Melting point 103–105 °C (217–221 °F; 376–378 K) (dec)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

MoOPH, also known as oxodiperoxymolybdenum(pyridine)-(hexamethylphosphoric triamide), is a reagent used in organic synthesis.[1] It contains a molybdenum(VI) center with multiple oxygen ligands, coordinated with pyridine and HMPA ligands, although the HMPA can be replaced by DMPU.[2] It is an electrophilic source of oxygen that reacts with enolates and related structures, and thus can be used for alpha-hydroxylation of carbonyl-containing compounds.[3] Other reagents used for alpha-hydroxylation via enol or enolate structures include Davis oxaziridine, oxygen, and various peroxyacids (see Rubottom oxidation). This reagent was first utilized by Edwin Vedejs as an efficient alpha-hydroxylating agent in 1974 and an effective preparative procedure was later published in 1978.[4]

  1. ^ a b c d Edwin Vedejs (April 15, 2001). "Oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide)". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ro022. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)
  2. ^ Paquette, Leo A.; and Koh Dongsoo (14 Sep 1992). "Explosion with MoO5-DMPU complex" (letter to the editor) in Chemical and Engineering News, p. 2.
  3. ^ "HYDROXYLATION OF ENOLATES WITH OXODIPEROXYMOLYBDENUM(PYRIDINE)(HEXAMETHYLPHOSPHORIC TRIAMIDE), MoO5·Py·HMPA(MoOPH): 3-HYDROXY-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPTAN-2-ONE". Organic Syntheses. 64: 127. 1986. doi:10.15227/orgsyn.064.0127.
  4. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).