138-24-9Relevant articles and documents
Selective monomethylation of primary amines with simple electrophiles
Lebleu, Thomas,Ma, Xiaolu,Maddaluno, Jacques,Legros, Julien
supporting information, p. 1836 - 1838 (2014/02/14)
Direct monomethylation of primary amines with methyl triflate was achieved with high selectivity (up to 96%). The key point of this single methyl transfer stems from the use of HFIP as the solvent that interferes with amines and avoids overmethylation.
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.
Alkylidene Transfer from Monochloroalkylmercury(II) Compounds to Aromatic Amines; Selective C-Alkylation
Barluenga, Jose,Campos, Pedro J.,Roy, Miguel A.,Asensio, Gregorio
, p. 1420 - 1426 (2007/10/02)
αα-Diarylalkane derivatives have been synthesized from monochloroalkylmercury(II) compounds in a noncarbenoid alkylidene transfer reaction which takes place selectively on the aromatic ring.A mechanism is suggested for this process.Intermediate products are prepared by alternative routes to ascertain their participation in the course of the reaction.As a consequence, two different aryl groups can be successively incorporated into the alkane molecule.