63620-76-8Relevant academic research and scientific papers
Acid-catalyzed synthesis of functionalized arylthio cyclopropane carbaldehydes and ketones
Porcu, Stefania,Luridiana, Alberto,Martis, Alberto,Frongia, Angelo,Sarais, Giorgia,Aitken, David J.,Boddaert, Thomas,Guillot, Regis,Secci, Francesco
, p. 13547 - 13550 (2019/01/06)
A general strategy for the synthesis of arylthio cyclopropyl carbaldehydes and ketones via a Br?nsted acid catalyzed arylthiol addition/ring contraction reaction sequence has been exploited. The procedure led to a wide panel of cyclopropyl carbaldehydes in generally high yields and with broad substrate scope. Mechanistic aspects and synthetic applications of this procedure were investigated.
REACTION OF α-BROMOCYCLOPROPYL PHENYL KETONES WITH LITHIUM THIOPHENOLATE BY A MECHANISM OF "LATENT" NUCLEOPHILIC SUBSTITUTION AT THE HALOGEN ATOM
Kulinkovich, O. G.,Tischenko, I. G.,Sviridov, S. V.,Divak, V. A.
, p. 880 - 885 (2007/10/02)
The reaction of E-1-benzoyl-1-bromo-2-phenylcyclopropane with lithium thiophenolate in THF leads to the formation of E-1-benzoyl-2-phenyl-1-phenylthiocyclopropane.Phenyl α-phenylthiocyclopropyl ketones are also produced with good yields by the action of s
Radical Cleavage and Competing Photoreactions of Phenacyl Sulfides
Wagner, Peter J.,Lindstrom, Michael J.
, p. 3062 - 3067 (2007/10/02)
The photochemistry of ketones with the stuctures PhCOCH2SR, PhCOCH2S(O)R, PhCOCH2SO2R, and p-X-PhCOCH2SPh has been studied.They all give primarily acetophenone as product when irradiated in the presence of benzenethiol, which traps free phenacyl radicals formed by excited state β-cleavage.The sulfur-centered radicals give coupling products.The maximum quantum yield for β-cleavage is 0.40; apparently 60percent of the initially formed radical pairs undergo in-cage reaction.When R = methyl or butyl, some acetophenone is formed by γ-hydrogen abstraction as well.Alkyl subtituents on the α-carbon enhance the disproportionation reactions of the phenacyl radicals.Measurements of quantum yields and triplet life times (by Stern-Volmer quenching of acetophenone formation) allowed determination of rate constants for β-cleavage as follows: PhS, 1E10-1E11; MeS(O), 6 * 1E9; BuS, 1.5 * 1E8; BuSO2, 1 * 1E7 s-1.Ring substituents increase triplet lifetimes.Absorption and phosphorescence spectra indicate that the n,?* and ?,?* transitions both involve some population of the C-S ?* orbital.This mixing, together with free spin density on the excited carbonyl carbon, appears to determine the rate constant for cleavage.Radical cleavage is also very fast and efficient for p-((phenylthio)methyl)acetophenone.
CYCLOHEXENOL ANNULATION VIA THE ALKOXY-ACCELERATED REARRANGEMENT OF VINYLCYCLOBUTANES
Danheiser, Rick L.,Martinez-Davila, Carlos,Sard, Howard
, p. 3943 - 3950 (2007/10/02)
The lithium and potassium salts of 2-vinylcyclobutanols undergo vinylcyclobutane rearrangement at 25-70 gradC, providing an efficient method for the synthesis of 3-cyclohexenol derivatives. 2-Vinylcyclobutanones are prepared from α,β-unsaturated carbonyl
