4519-33-9Relevant articles and documents
The Tetraethylphosphorodiamidate (OP(O)(NEt2)2) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement
Alessi, Manlio,Patel, Jignesh J.,Zumbansen, Kristina,Snieckus, Victor
supporting information, p. 2147 - 2151 (2020/03/13)
We report on the tetraethylphosphorodiamidate (-OP(O)(NEt2)2) group as an effective directed metalation group (DMG). Lithiation-electrophile quench of 1 provides a general synthesis of ortho-substituted aryl and naphthyl phosphorodiamidates 4-8. We also describe the phospha anionic ortho-Fries (AoF) rearrangement of the phosphorodiamidates 1a,1ba2 or 3 and its vinylogous counterpart to the ortho-tolyl phosphorodiamidates 5ba 13. Intermolecular competition experiments demonstrate the approximately equal DMG strength of the-OP(O)(NEt2)2 and the most powerful OCONEt2 groups.