113446-18-7Relevant academic research and scientific papers
Intermolecular scandium triflate-promoted nitrene-transfer [5 + 1] cycloadditions of vinylcyclopropanes
Laudenschlager, Julie E.,Combee, Logan A.,Hilinski, Michael K.
, p. 9413 - 9417 (2019)
Sc(OTf)3-promoted [5 + 1] cycloaddition of vinylcyclopropanes with PhINTs is reported, enabling the regioselective preparation of a range of 1,2,3,6-tetrahydropyridine scaffolds under mild conditions. This represents the second example of a [5
A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via suzuki-type coupling of acid chlorides with cyclopropylboronic acids.
Chen,Deng
, p. 1649 - 1651 (2007/10/03)
[reaction: see text] The palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with acyl chlorides was achieved by the combination of Ag(2)O and K(2)CO(3) as the base. Highly enantiomerically enriched cyclopropyl ketones (ee >90%) were also obtained by the reaction of corresponding chiral cyclopropylboronic acids.
OPENING OF THE CYCLOPROPANE RING IN α-BROMOCYCLOPROPYL KETONES BY THE ACTION OF TRIPHENYLPHOSPHINE
Kulinkovich, O. G.,Tischenko, I. G.,Sviridov, S. V.
, p. 885 - 888 (2007/10/02)
The reaction of a series of α-bromocyclopropyl ketones substituted in the three-membered ring with triphenylphosphine in alcohols in the presence of catalytic amounts of hydrochloric acid leads to the formation of the products from opening of the cyclopropane ring.Under analogous conditions 1-benzoyl-1-bromocyclopropane undergoes reductive dehalogenation.In boiling methanol 7-exo-benzobicycloheptane is converted into trans-1-bromo-2-benzoylmethylcyclohexane by the action of a mixture of triphenylphosphine and 1-benzoyl-1-bromocyclopropane and also by a mixture of triphenylphosphine and carbon tetrabromide.
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.
