98098-45-4Relevant academic research and scientific papers
ALLYLIC REARRANGEMENT OF CYANOPHOSPHATE. II. SYNTHESIS OF β-CYANO-α,β-UNSATURATED KETONES
Kurihara, Takushi,Miki, Masuo,Yoneda, Ryuji,Harusawa, Shinya
, p. 2747 - 2753 (2007/10/02)
Boron trifluoride-catalyzed allylic rearrangement of the cyanophosphates of α,β-unsaturated ketones (1a-d, 7 and 14) was found to give the allylic phosphates (3a-d, 9 and 16), which were successfully converted to β-cyano-α,β-unsaturated ketones (6a-d, 13 and 20) by acid hydrolysis (0.5 N HCl) followed by manganese dioxide oxidation of the resulting allylic alcohols(5a-d, 11, 12 and 17).The stereochemical features of the allylic phosphates (9 and 16) are discussed.Keywords-α,β-unsaturated ketone; diethyl phosphorocyanidate; cyanophosphate; allylic rearrangement; boron trifluoride etherate; manganese dioxide; β-cyano-α,β-unsaturated ketone
ALLYLIC REARRANGEMENT OF α,β-UNSATURATED KETONE-DIETHYL PHOSPHOROCYANIDATE ADDUCTS
Harusawa, Shinya,Miki, Masuo,Yoneda, Ryuji,Kurihara, Takashi
, p. 2164 - 2167 (2007/10/02)
α,β-Unsaturated ketones react with diethyl phosphorocyanidate in the presence of lithium cyanide to give α-diethylphosphonooxy nitriles which are transformed into conjugated allylic phosphates via a novel boron trifluoride etherate-catalyzed allylic rearrangement.
