111571-80-3Relevant academic research and scientific papers
Allylic Rearrangement of Cyanophosphates. III. Reaction of Acyclic Enone Cyanophosphates
Kurihara, Takushi,Miki, Masuo,Santo, Kazunori,Harusawa, Shinya,Yoneda, Ryuji
, p. 4620 - 4628 (2007/10/02)
Boron trifluoride-catalyzed allylic rearrangement of α,β-unsaturated ketone cyanophosphates (2, 6 and 12) gave (Z)-4-diethylphosphonooxy-2-butenenitriles (3, 8 and 13), while α,β-unsaturated aldehyde cyanophosphates (17a-c) afforded (E)-4-diethylphosphonooxy-2-butenenitriles (18a-c) stereoselectively.The stereo- and regioselective reaction of 2 with several kinds of aromatics in the presence of boron trifluoride etherate afforded (Z)-4-aryl-2-methyl-2-butenenitriles (20) via the SN2' reaction.On the other hand, treatment of 2 with 1-substituted indoles in the presence of boron trifluoride etherate gave 1-amino-2-methylcarbazole derivatives (23a-c).Keywords-α,β-unsaturated ketone; α,β-unsaturated aldehyde; cyanophosphate; allylic rearrangement; boron trifluoride etherate; 2-butenenitrile derivative; SN2' reaction; 1-aminocarbazole derivative
