Product Details of 150-19-6. In 2020.0 ORG LETT published article about STEREOSELECTIVE P-O; ORTHO-LITHIATION; BIS(DIMETHYLAMINO)PHOSPHORYL GROUP; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; C REARRANGEMENT; MIGRATION; PHENOLS; OLEFINS; ROUTES in [Alessi, Manlio; Patel, Jignesh J.; Zumbansen, Kristina; Snieckus, Victor] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada in 2020.0, Cited 58.0. The Name is m-Methoxyphenol. Through research, I have a further understanding and discovery of 150-19-6.
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,1b -> 2 or 3 and its vinylogous counterpart to the ortho-tolyl phosphorodiamidates 5b -> 13. Intermolecular competition experiments demonstrate the approximately equal DMG strength of the -OP(O)(NEt2)(2) and the most powerful OCONEt2 groups.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles