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A New Route to Phosphoryl Thiocarbonyl Mixed Imides - Structure Limitations
Authors:Kenneth E Debruin  Eric E Boros
Institution:Department of Chemistry , Colorado State University , Fort Collins, Colorado, 80523
Abstract:Abstract

The rearrangement of N-methyl thiophosphoryl carbonyl mixed imides (I, XYP(S)N(Me)C(O)Z) to N-methyl phosphoryl thiocarbonyl mixed imides (II, XYP(O)N(Me)C(S)Z) was studied as a function of substitution on phosphorus (Ia: X = Y = MeO; Ib: X = Ph, Y = MeO; and Ic: X = Y = Ph) with Z = Ph and as a function of substitution on carbon (Ia: Z = Ph; Id: Z = Me; and Ie: Z = OiBu) with X = Y = MeO. For Ia, Ib, and Id, rearrangement is complete and quantitative. In contrast, Ic rearranges to a 10/90 equilibrium mixture of IIc/Ic and Ie gives no evidence for rearrangement to the phosphoryl thiocarbonyl mixed imide IIe. A relative reactivity order for Ia, Ib, Ic, and Id of 1.00, 0.15, 0.036, and 0.11 respectively, was observed in the rearrangements.
Keywords:4-halo-1  3  5  7-tetramethyl-1  3  5  7-tetraaza-4Δ5-phosphaspiro [3  3]heptane-2  6- diones  X-ray structures
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