The Tetraethylphosphorodiamidate (OP(O)(NEt2)2) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement was written by Alessi, Manlio;Patel, Jignesh J.;Zumbansen, Kristina;Snieckus, Victor. And the article was included in Organic Letters in 2020.Application of 19311-91-2 This article mentions the following:
We report on the tetraethylphosphorodiamidate (-OP(O)(NEt2)2) group as an effective directed metalation group (DMG). Directed ortho-lithiation-electrophile quench of ArOP(O)(NEt2)2 (1a–e; Ar = substituted Ph, 2-naphthyl) provides a general synthesis of ortho-substituted aryl and naphthyl phosphorodiamidates. We also describe the phospha anionic ortho-Fries (AoF) rearrangement of the phosphorodiamidates 1a,b, giving phosphonates 3-R-2-[P(O)(NEt2)2]C6H3OH its vinylogous counterpart to the ortho-tolyl phosphorodiamidates. Intermol. competition experiments demonstrate the approx. equal DMG strength of the -OP(O)(NEt2)2 and the most powerful OCONEt2 groups. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application of 19311-91-2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Application of 19311-91-2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics