24619-07-6Relevant academic research and scientific papers
PHOSPHORUS-NITROGEN COMPOUNDS. PART 48. THE REACTIONS OF N,N-DIMETHYLTOLUIDINES WITH PHOSPHORUS(V) CHLORIDES. FORMATION OF A NOVEL HETEROCYCLIC SYSTEM.
Cheng, Ching Yee,Shaw, Robert A.
, p. 185 - 192 (2007/10/02)
The reactions of phosphorus oxychloride, P(O)Cl3, with the three N,N-dimethyltoluidines have been studied.O-toluidine gave after suitable work-up only a "nitrogen-substituted" derivative, P(O)(NMeC6H4Me-2)(OEt)2, whilst the m-analogue gave both "nitrogen-substituted", P(O)(NMeC6H4Me-3)(OEt)2, and "carbon-substituted" products, P(O)(C6H3Me-2-NMe2-4)2(OEt), as well as two purely organic compounds, CH2(C6H3Me-2-NMe2-4)2 and CH(C6H3Me-2-NMe2-4)3.With N,N-dimethyl-p-toluidine in addition to two acyclic 'nitrogen-substituted' products, P(O)(NMeC6H4Me-4)(OEt)2 and P(O)(NMeC6H4Me-4)2(OEt), the chloro- and ethoxy-derivative of a novel eight-membered heterocyclic system, P(O)X (X = Cl or OEt), as well as two organic products, CH2(C6H3Me-5-NHMe-2)2 and CH2(C6H3Me-5-NMe2-2)-(C6H3Me-5-NHMe-2) were isolated.The reaction of thiophosphoryl chloride, P(S)Cl3, with N,N-dimethyl-p-toluidine also gave a similar heterocycle, P(S)Cl.The 1H NMR spectra are discussed and related to the X-ray crystal structures.
