Organophosphorus derivatives of methylurethan

Synthesis of intermediate compounds with P-N bond from (thio)carbamates and chlorodioxaphospholanes and -phosphorinanes and their reactivity

“…Alternatively -caprolactam can be used [15]. In the latter case [15] it is supposed that the reaction proceeds via intermediate formation of a five membered complex.…”

“…In the latter case [15] it is supposed that the reaction proceeds via intermediate formation of a five membered complex. Interestingly, in earlier work [13], also phosphorylated carbamates with P-N(R)-C(O)OR motifs were synthesized, including 2-(N-ethoxycarbonyl methylamino)-l,3,2-dioxaphospholane (6), diethyl N-ethoxycarbonyl-N-methylphosphoramidite (7) and 4,5-benzo-2-(N-ethoxycarbonymethylamino)-1,3,2-dioxaphospholane (8) (Figure 2).…”

“…Interestingly, in earlier work [13], also phosphorylated carbamates with P-N(R)-C(O)OR motifs were synthesized, including 2-(N-ethoxycarbonyl methylamino)-l,3,2-dioxaphospholane (6), diethyl N-ethoxycarbonyl-N-methylphosphoramidite (7) and 4,5-benzo-2-(N-ethoxycarbonymethylamino)-1,3,2-dioxaphospholane (8) (Figure 2). N-phosphorylated methylcarbamates, in turn, were shown to react with elemental sulfur [9,15]. The products possess insecticidal activity resulting, however, in burns of the leaves.…”

“…The products possess insecticidal activity resulting, however, in burns of the leaves. Chloroanhydrides can also react with compound 7 [15].…”