CONFORMATIONS OF SATURATED SIX-MEMBERED-RING PHOSPHORUS HETEROCYCLES SYNTHESES AND X-RAY CRYSTAL STRUCTURES OF TWO 2-(DIMETHYLAMINO)-2-OXO-3-ARYL-5,5-DIMETHYL-1,3,2-OXAZAPHOSPHORINANES
- 1 March 1991
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 57 (1) , 37-49
- https://doi.org/10.1080/10426509108038829
Abstract
The crystal and molecular structures have been determined for 2-(dimethylamino)-2-oxo-3-(4-fluoro-phenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane, 1, and 2-(dimethylamino)-2-oxo-3-(4-dimethylami-nophenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane, 2. Compound 1 crystallizes in the monoclinic space group P21/c with eight molecules per unit cell (2 crystallographically independent molecules) of dimensions a=17.251(1) Å, b=10.822(3) Å, c=18.075(6) Å, and β=118.20(2)°. Compound 2 crystallizes in the monoclinic space group P21/a with Z=4, a=14.148(7) Å, b=6.907(4) Å, c=17.210(6) Å, and β=94.33(3)°. Full-matrix least-squares refinement of these structures converged at R=0.0469 and R=0.0581 for 1 and 2, respectively. Both compounds adopt chair conformations in the solid state with equatorially disposed dimethylamino substituents on phosphorus.Keywords
This publication has 19 references indexed in Scilit:
- Conformations of saturated six-membered ring phosphorus heterocycles. 2-Aryl-1,3,2-.lambda.5-oxazaphosphorinanesJournal of the American Chemical Society, 1988
- Conformations of saturated six-membered ring phosphorus heterocycles. Chair-chair equilibria for cyclophosphamide, the 5,5-dimethyl derivative, and related 1,3,2-oxazaphosphorinanes. Relative conformational energies of nitrogen mustard and other R2N groups attached to phosphorusJournal of the American Chemical Society, 1985
- Conformations of saturated six-membered-ring phosphorus heterocycles. Axial, nonplanar dimethylamino group of 5,5-dimethyl-2-(dimethylamino)-2-oxo-1,3,2-oxazaphosphorinane as determined by x-ray crystallography. Proton NMR and IR spectroscopic analysis of conformation in solutionJournal of the American Chemical Society, 1984
- Conformations of saturated six-membered phosphorus heterocycles. X-ray crystallographic and proton NMR study of cis-2-oxo-2-(dimethylamino)-5-phenyl-1,3,2-oxazaphosphorinane, a cyclophosphamide-like molecule in a twist conformationJournal of the American Chemical Society, 1984
- Conformations of saturated six-membered ring phosphorus heterocycles. cis- and trans-2-oxo- and -2-thio-2-(dimethylamino)-5-tert-butyl-1,3,2 .lambda.5-oxazaphosphorinanes: molecules related to cyclophosphamideJournal of the American Chemical Society, 1982
- 4 Cyclophosphamide AnaloguesProgress in Medicinal Chemistry, 1982
- Cyclophosphamide and its congenersPublished by Royal Society of Chemistry (RSC) ,1982
- X-ray structure and absolute configuration of (−)-(2S,4R)-4-methycyclophosphamide {2-[bis(2-chloroethyl)amino]-4-methyltetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide}Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1981
- X-ray and NMR studies of a cyclophosphamide-like molecule, cis-2-oxo-2-dimethylamino-3-phenyl-5-tert-butyl-1,3,2-oxazaphosphorinane. Twist conformation in both solid phase and in solutionJournal of the American Chemical Society, 1979
- Stereochemical aspects of phosphorus‐containing cyclohexanesPublished by Wiley ,1979