1007-80-3Relevant articles and documents
Vogt,Siegfried
, p. 1779,1789 (1976)
Rate and product studies in the solvolyses of two cyclic phosphorochloridate esters
Koh, Han Joong,Kang, Suk Jin,Kevill, Dennis N.
, p. 1404 - 1415 (2010)
Kinetic and product studies of the solvolyses of acyclic phosphorochloridates are extended to two cyclic diesters, 2-chloro-1,3,2- dioxaphospholane-2-oxide (1) and 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane- 2-oxide (2). Slightly faster solvolyses are observed for 1 than for the acyclic dimethyl phosphorochloridate (3), and 2 solvolyzes somewhat slower than 3. An extended Grunwald-Winstein equation treatment shows similar sensitivities to changes in solvent nucleophilicity and solvent ionizing power for 1, 2, and 3, and a concerted SN2 attack is proposed in each case. Product studies for the solvolyses of 2 in aqueous alcohols are presented. [image presented]. Copyright Taylor & Francis Group, LLC.
2-Alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones α-Lithiated Carbanions. Synthesis, Stability, and Conformation
Patois, Carl,Ricard, Louis,Savignac, Philippe
, p. 1577 - 1581 (2007/10/02)
The preparation and a conformational study of lithiated 2-alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones (2) in THF-hexane are described.These anions are present as two rapidly interconverting species with the P=O bond either axial (2a) or equatorial (2e).They are thermally unstable, but can be stabilised by the presence of one equivalent of LiBr or of lithium di-isopropylamide.A 31P NMR study of the self condensation of the carbanions (2) showed that the phosphorus atom in the axial conformation (2a) is more electrophilic than in the equatorial one (2e).An X-ray structural study of 2,5,5-trimethyl-1,3,2-dioxaphosphorinan-2-one is described.