104283-60-5Relevant academic research and scientific papers
PALLADIUM(0) CATALYZED AZIDATION AND AMINATION OF ALLYL ACETATES. SELECTIVE SYNTHESIS OF ALLYL AZIDES AND PRIMARY ALLYLAMINES
Murahashi, Shun-Ichi,Tanigawa, Yoshio,Imada, Yasushi,Taniguchi, Yuki
, p. 227 - 230 (1986)
Palladium catalyzed reaction of allyl acetates with azide ion gives allyl azides, which are readily converted into the corresponding primary allylamines upon treatment with PPh3/NaOH.
Palladium(0)-Catalyzed Azidation of Allyl Esters. Selective Synthesis of Allyl Azides, Primary Allylamines, and Related Compounds
Murahashi, Shun-Ichi,Taniguchi, Yuki,Imada, Yasushi,Tanigawa, Yoshio
, p. 3292 - 3303 (2007/10/02)
Palladium(0)-catalyzed reaction of allyl esters such as phosphates, carbonates, and carboxylates with sodium azide gives allyl azides.The azidation proceeds with retention of configuration at the allylic carbon.Optically active (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide (19) is obtained from (R)-(E)-(+)-4-phenyl-3-buten-2-yl acetate (18) stereoselectively.Sequential substitution of (Z)-4-acetoxy-2-buten-1-yl diethyl phosphate (24) with nucleophiles and subsequently azide ion gives (E)-4-substituted-2-buten-1-yl azides 27.The reaction of allyl azides with triphenylphosphine gives iminotriphenylphosphoranes, which are versatile synthetic intermediates of primary allylamines, N-allylamines, and N-allylamides.Treatment of allyl azides with triphenylphosphine and subsequently with aqueous ammonium solution gives primary allylamines.Other synthetic applications of allyl azides are also described.
