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.
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.
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
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
