REACTION OF TRISDIALKYLAMINOPHOSPHINES WITH AROMATIC ALDEHYDES .I. NITROBENZALDEHYDES . FORMATION OF 2,2,2-TRISAMINO-1,3,2-DIOXAPHOSPHOLANES AND THEIR CONVERSION INTO EPOXIDES

The phosphorus of trisdialkylaminophosphines attacked the carbonyl oxygen of o-, m-, and p-nitrobenzaldehydes. The resulting 1:1 adducts with P-O-C bonds added to a second molecule of the aldehyde and formed 2:1 adducts. The 2:1 adducts were isolated as stable 2,2,2-triamino-1,3,2-dioxaphospholanes in the case of fivemembered cyclic trisdialkylaminophosphines. These phosphoranes were converted at 80° into dinitrostilbene oxides and the amidates with inversion of configuration at carbon. The 2:1 adducts derived from open-chain trisdialkylaminophosphines were unstable even below 0° and gave the dinitrostilbene oxides. The P31 nmr shifts are described. © 1968, American Chemical Society. All rights reserved.