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The molecular and crystal structure of endo-2-methyl-7-hydroxy-7-oxo-N-phenyl-7-phosphabicyclo-[2.2.1] hept-2-ene-5,6-dicarboximide
Authors:M W Wieczorek  G D Bujacz  R Bodalski  Louis D Quin
Institution:(1) Institute of Technical Biochemistry, Technical University of Lstrokódzacute, Stefanowskiego 4/10, 90-924 Lstrokódzacute, Poland;(2) Institute of Organic Chemistry, Technical University of Lstrokódzacute, Zwirki 36, 90-924 Lstrokódzacute, Poland;(3) Department of Chemistry, University of Massachusetts, 01003 Amherst, Massachusetts
Abstract:The structure of the title compound1 has been determined by X-ray crystallography analysis. The following crystal data were found: orthorhombic,Pca2l,a=9.60691),b=16.356(1),c=8.686(1) angst. Both the phospholane and phospholene rings involved in the 7-phosphabicyclo-2.2.1] hept-2-ene system have almost regular envelope conformations, and the cyclohexene ring has a significantly deformed boat conformation. The low value of the C–P–C angle, 84.2(2)°, reflects the steric strain around the phosphorus bridge and may be responsible for the reactivity of esters and amides derived from1 in the O-insertion reaction with m-chloro-perbenzoic acid. The dihedral angle between the plane of the benzene and succinimide rings is 82.4(2)°.
Keywords:Structure C15H14NO4P  Baeyer-Villiger reaction
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