80401-32-7Relevant academic research and scientific papers
STEREOCHEMISTRY OF SUBSTITUTION AT TRICOVALENT PHOSPHORUS
Dahl, Otto
, p. 3281 - 3284 (1981)
Reactions of one diastereomer of a =P-NMe2 compound (1a) with alcohols, phenol and amines have been shown by NMR to proceed with initial inversion at phosphorus, but the overall reactions are not stereoselective.
Stereochemistry of Substitution at Trico-ordinate Phosphorus
Nielsen, John,Dahl, Otto
, p. 553 - 558 (2007/10/02)
A series of reactions of ring-substituted 1,3,2-dioxaphospholanes, 1,3,2-oxazaphospholanes, 1,2-oxaphospholes, and phosphetanes bearing the leaving groups Cl, OR, or NR2 on phosphorus, with the nucleophiles HCl, MeO-, MeOH, PhOH, Me2NH, Et2NH, and 5NH have been studied.N.m.r. signals (1H and 31P) from reactant and product diastereoisomers have been assigned, and the stereochemistry of the substitution reactions have been determined by 31P n.m.r. monitoring.The outcome varies from complete inversion to complete lack of stereoselectivity.During the initial stages many of the non-selective reactions proceed with predominant inversion, and most of the results may be interpreted by assuming that the actual substitution step occurs with inversion, and that the lack of stereoselectivity is due to competing isomerizations of products or reactants.Exceptions are certain reactions where the leaving group is Cl; these appear to involve a non-selective substitution step.
