106914-17-4Relevant articles and documents
Contraste entre la phosphorylation des alcools et des amines par les 2-4 dioxo, oxa-1, aza-3 phospholanes-2
Mulliez, Michel,Wolf, Robert
, p. 101 - 108 (2007/10/02)
Three new heterocycles 4 were synthesised either by reaction of the dichlorides 7 with the α hydroxyamide 8 in presence of two equivalents of silves tetrafluoroborate in pyridine (fig. 3), or by a hexamethyldisilazane promoted cyclization of the phosphoramide 12a (fig. 4), or by oxidation with Corey's reagent of the corresponding P(III) heterocycle 15 (fig. 5); phosphoranes 9 (fig. 3) and 16 (fig. 5) being formed as by products.Alcohols were easily phosphorylated with opening of the heterocycles 4 and rupture of the P2-N3 bond, after that of the exocyclic P-OPh bond in the case of 4b.Amines however, depending on the R1 substituent at phosphorus, either do not react (R1=Ph) or are axclusively phosphorylated with retention of the cyclic structure (R1=PhO).An explanation is proposed.
