89619-13-6Relevant academic research and scientific papers
Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols
Capel, Estefania,Rodríguez-Rodríguez, Marta,Uria, Uxue,Pedron, Manuel,Tejero, Tomas,Vicario, Jose L.,Merino, Pedro
supporting information, p. 693 - 707 (2022/01/04)
The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with N-bromosuccinimide has been experimentally and computationally studied. The reaction yields highly enantioenriched cyclopenta
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
Alazet, Sebastien,Preindl, Johannes,Simonet-Davin, Raphael,Nicolai, Stefano,Nanchen, Annik,Meyer, Thierry,Waser, Jerome
supporting information, p. 12334 - 12356 (2018/09/27)
Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.
Intermolecular Carboamination of Unactivated Alkenes
Zhang, Yu,Liu, Haidong,Tang, Luning,Tang, Hai-Jun,Wang, Lu,Zhu, Chuan,Feng, Chao
, p. 10695 - 10699 (2018/09/06)
Herein, we report the first example of group transfer radical addition of O-vinylhydroxylamine derivatives onto unactivated alkenes. By utilizing O-vinylhydroxylamine derivatives as both the N- and C-donors, this reaction enables intermolecular carboamination of unactivated alkenes in an atom economical fashion. As the process is initiated through N-radical addition followed by C-transfer, linear carboamination products are afforded. This differs from canonical radical carbofunctionalization of olefins, which typically favors branched product owing to initiation by C-radical addition.
The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity
Weiss, Hilton M.,Touchette, Kim M.,Angell, Sarah,Khan, Jihan
, p. 2152 - 2156 (2007/10/03)
In a weakly acidic solution, the addition of HBr to 1-phenylprop-1-yne produces predominantly the anti-Markovnikov product. In this paper, we consider five possible explanations for this behavior and conclude that the concerted addition is occurring on the acetylenic π bond orthogonal to the extended aromatic π system. The electronic effect of the distal methyl group and the steric hindrance of the coplanar phenyl ring combine to promote bromide attack at the β carbon. Attack on this π bond is insensitive to the electronic effect of meta and para substituents on the ring but is very (sterically) sensitive toward all ortho substituents.
Effect of the α-Trifluoromethyl Moiety on the Solvolysis of Allylic Sulfonates
Gassman, Paul G.,Harrington, Clinton K.
, p. 2258 - 2273 (2007/10/02)
A series of allylic sulfonates bearing aryl substituents on the 2-position and/or trifluoromethyl groups on the 1- and/or 3-positions has been studied under solvolytic conditions in 2,2,2-trifluoroethanol.Nonarylated 1,3-di(trifluoromethyl)-substituted allylic sulfonates did not solvolyze in a conventional manner but instead gave products diagnostic of a complex isomerization-cleavage process.Mono(trifluoromethyl)-substituted allylic sulfonates solvolyzed by normal paths to give kH/kCF3 ratios of 2E6 and 4E4 for the substitution at the 1- and 3-positions, respectively.No evidence for 1,3-? interactions was discerned.
