4921-73-7Relevant articles and documents
New routes to diethyl 1-alkenylphosphoramidates
Napieraj, Anna,Zawadzki, Stefan,Zwierzak, Andrzej
, p. 6299 - 6305 (2007/10/03)
New routes to N-(diethoxyphosphoryl)imines derived from enolizable carbonyl compounds have been investigated. Three different procedures were studied: (i) the aza-Claisen condensation of ethyl-[N-(diethoxyphosphoryl)]-formimidate with enolizable ketones, (ii) the reaction between diethyl N-sulfinylphosphoramidate and aliphatic aldehydes, and (iii) the thermally induced reaction of diethyl phosphoramidate with ketone diethyl acetals. With two exceptions in all cases the products were identified as diethyl 1-alkenylphosphoramidates with no spectroscopically detectable amounts of imine tautomers. The aza-Claisen condensation can be recommended as a simple and effective route to diethyl 1-alkenyl-3-oxophosphoramidates. (C) 2000 Elsevier Science Ltd.
Reactivity and diastereoselectivity in the thermal and Lewis acid- catalyzed Diels-Alder reactions of N-sulfinylphosphoramidates
Zhang,Flann
, p. 1372 - 1378 (2007/10/03)
The [4 + 2] cycloaddition reactions of N-sulfinylphosphoromidates, prepared from the corresponding phosphoramidates by treatment with N- (chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (> 95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as Well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.