New cyclic phosphonium salts derived from the reaction of phosphine-aldehydes with acid

作者：Mikhailine Alexandre A; Lagaditis Paraskevi O; Sues Peter E; Lough Alan J; Morris Robert H^*

来源：Journal of Organometallic Chemistry, 2010, 695(14): 1824-1830.

DOI：10.1016/j.jorganchem.2010.04.016

• Ligand design
• Phosphorus
• Macrocycles
• Aldehyde
• Deprotection

Various cyclic phosphonium structures are formed in high yield by the deprotection of unstable phosphine-aldehydes in acidic solution. When there is a methylene spacer between the phosphine and the aldehyde, a phosphonium ion [PHR2CH2CH(OEt)(2)]Br-2, R= iPrOH, Et is obtained. Reaction of these phosphonium salts with water produces the dimers [-PR2CH2CH(OH)-](2)[Br](2) R = iPr, Et. When there is an ethylene spacer as in PPh2CH2CH2CH(OCH2CH2O), a remarkable tetramer with a 16-membered ring [-PPh2CH2CH2CH (OH)-](4)[Cl](4) forms as one diastereomer in hydrochloric acid solution. Reaction of HCl with the protected phosphine-aldehyde with a propylene spacer (PPh2CH2CH2CH2CH(OCH2CH2O)) results in the formation of the monomeric phosphonium salt [-PPh2 CH2CH2CH2CH(OH)-] Cl with a 5-membered ring. Solid state structures of different ring types were determined using X-ray diffraction experiment.

• 出版日期2010-6-15