185069-60-7

Upstream product

• 109-72-8 n-butyllithium 
• 77121-88-1 (S)-3,3,3',3'-tetrakis(trifluoromethyl)-1,1'-spirobi<3H,2,1λ⁵-benzoxaphosphole> 

Downstream Products

• 183946-56-7 [TBPY-5-15]-1,1,1,3,3,3-hexafluoro-2-{2-[1-butyl-3,3-bis(trifluoromethyl)-1,3-dihydro-2,1λ⁵-benzoxaphosphol-1-yl]phenyl}propan-2-ol 

Relevant academic research and scientific papers

Synthesis and characterization of intra- and intermolecular hydrogen bonding isomers of P-H (apical) phosphoranes bearing a hydroxyl group and their thermal cyclization

The reaction of spirophosphorane 1 with 3 equivalents of RLi (R=Me, n-Bu, t-Bu) in Et2O at -78°C followed by treatment with aq. HCl gave monocyclic P-H phosphoranes 2-4 bearing an apical hydrogen atom in good yields. Particularly in the case of 4, an isomer 4a with intramolecular hydrogen bonding and an isomer 4b with intermolecular hydrogen bonding with a solvent molecule could be separately isolated. Monocyclic phosphoranes 2-4 cyclized intramolecularly with elimination of H2 to form spirophosphoranes 5-7 upon heating. Kinetic examination of cyclizations implied that they proceed via four-membered ring transition states involving hexacoordinate phosphorus.