Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent

• Published in: Synlett no. 15; pp. 2335 - 2336
• Main Authors: El Kaim, L, Gaultier, L, Grimaud, L, Dos Santos, A
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 19.09.2005
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Pudovik reaction; phospha-Brook rearrangement; dialkylphosphite; ACID-ESTERS; phosphate esters

Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosp...