140458-23-7Relevant academic research and scientific papers
Diastereoselective and intramolecular cycloadditions of asymmetric P-nitroso phosphine oxides
Ware Jr., Roy W.,Day, Cynthia S.,King, S. Bruce
, p. 6174 - 6180 (2007/10/03)
Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an N-O heterodienophile with 1,3-cyclopentadiene to give the diastereomeric cycloadducts 6a,b in a ratio of 1.5:1 (6a:6b). The same reaction in the presence of tin tetrachloride produces 6a,b in a ratio of 2.9:1 (6a:6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1,3-cyclopentadiene forms the diastereomeric cycloadducts 16a,b in a ratio of 3.1:1 (16a:16b). These results suggest the reactions of these P-nitroso phosphine oxides and 1,3-cyclopentadiene occur through a transition state where the heterodienophile adopts an s-cis conformation and approaches the diene in an exo fashion syn to the phenyl group. This model resembles those proposed for the cycloadditions of the structurally similar asymmetric vinyl phosphine oxides. Reaction of 18 with 1,3-cyclopentadiene in the presence of a Lewis acid produces cycloadducts 16a,b in a ratio of 7:1 (16a:16b), which approaches synthetic utility. Similar experiments show that 1,3-cyclohexadiene likely reacts with P-nitroso phosphine oxides through a different transition state, limiting current predictions regarding the diastereo-selectivity of these reactions. The intramolecular cycloaddition of an asymmetric P-nitroso phosphine oxide (19) for the first time produces a unique phosphorus-containing heterocyclic compound (20).
Stereospecificity in the Rearrangement Reactions of an N-Phosphinoyl-O-sulfonylhydroxylamine with Methylamine and tert-Butylamine: Retention of Configuration at Phosphorus as Evidence for the Initial Formation of a Phosphonamidic Sulfonic Mixed Anhydride
Harger, Martin J. P.,Sreedharan-Menon, Ramesh
, p. 3261 - 3268 (2007/10/02)
Reaction of the N-phosphinoyl-O-sulfonylhydroxylamine PhMeCH(Ph)P(O)NHOMs 10 with RNH2 (R = Me or t-Bu) results in migration of the phenyl group from phosphorus to nitrogen which leads to the rearrangement product PhMeCHP(O)(NHPh)NHR.Using samples of 10 e
