108401-97-4Relevant articles and documents
Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation
Ren, Xinyi,Shen, Chaoren,Wang, Guangzhu,Shi, Zhanglin,Tian, Xinxin,Dong, Kaiwu
supporting information, p. 2527 - 2532 (2021/05/05)
Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.
COMPETITION OF REDUCTIVE DEHALOGENATION, ABSTRACTION-ADDITION, AND FAVORSKII REARRANGEMENT IN THE REACTION OF α-BROMOCYCLOPROPYL KETONES WITH SODIUM ALCOHOLATES
Kulinkovich, O. G.,Tishchenko, I. G.,Sviridov, S. V.
, p. 1275 - 1280 (2007/10/02)
Oxidation of the corresponding α-bromocyclopropylcarbinols gave 7-exo-bromo-7-endo-benzoylbicycloheptane, E-1-bromo-1-benzoyl-2-phenylcyclopropane, E-1-bromo-1-benzoyl-2-butylcyclopropane, E-1-bromo-1-acetyl-2-phenylcyclopropane, and 7-exo-bromo-7-endo-acetylbicycloheptane and the reactions of these compounds with sodium alcoholates were studied.Depending on the structure of the starting α-bromocyclopropyl ketone, the alcoholate used, and the solvent, the predominant reaction is reductive dehalogenation, Favorskii rearrangement or abstraction-addition.In the latter case, 2-alkoxycyclopropyl ketone intermediates are isomerized to 4,5-dihydrofuran derivatives.
