37555-48-9Relevant academic research and scientific papers
Platinum complex-catalyzed hydrosilylation of 2,2-diaryl-1-methylenecyclopropane affording (silylmethyl)cyclopropane
Nishihara, Yasushi,Itazaki, Masumi,Osakada, Kohtaro
, p. 2059 - 2061 (2002)
PtI2(PPh3)2-catalyzed hydrosilylation of 2,2-diphenyl-1-methylenecyclopropane with HSiEt3 forms (2,2-diphenylcyclopropyl)methyl(triethyl)silane in 87% yield as a sole product. This highly selective addition of S
Drastic Effects of Dioxygen on the Selectivity of Reduction by LiAlH4. Milder Conditions Made Possible by Strictly Anaerobic Conditions
Peralez, Eric,Negrel, Jean-Claude,Chanon, Michel
, p. 6457 - 6460 (1995)
Reduction of the gem-disubstituted cyclopropane 1 with LiAlH4 yields different results under strictly anaerobic conditions and loosely anaerobic ones.Under strictly anaerobic conditions, (+)-1-bromo-2,2-diphenylcyclopropanecarbinol 2 is quantitatively red
Diazo- And transition-metal-free C-H insertion: A direct synthesis of β-lactams
Gomes, Luis F. R.,Veiros, Ls F.,Maulide, Nuno,Afonso, Carlos A. M.
, p. 1449 - 1453 (2015/01/30)
Carbene intermediates are very useful species for a range of reactions including C-H insertions and cycloadditions. They are most commonly generated by metal-catalyzed release of nitrogen gas from diazo precursors. Herein, we present a novel C-H insertion
Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes
Otte, Douglas A. L.,Woerpel
supporting information, p. 3906 - 3909 (2015/08/18)
Addition of allylmagnesium reagents to an aliphatic aldehyde bearing a radical clock gave only addition products and no evidence of ring-opened products that would suggest single-electron-transfer reactions. The analogous Barbier reaction also did not pro
Aryl-substituted cyclopropyl acetylenes as sensitive mechanistic probes in the gold-catalyzed hydration of alkynes. comparison to the Ag(I)-, Hg(II)-, and Fe(III)-catalyzed processes
Velegraki, Georgia,Stratakis, Manolis
, p. 8880 - 8884 (2013/09/24)
The gold-catalyzed hydration of 2-phenyl- or 2,2-diphenylcyclopropyl acetylene, sensitive probes to trace the formation of vinyl carbocations, provides exclusively the corresponding cyclopropyl methyl ketones. On the other hand, in the Ag(I)- or Fe(III)-c
SmI2-mediated reductive cross-coupling reactions of -cyclopropyl nitrones
Burchak, Olga N.,Masson, Geraldine,Py, Sandrine
scheme or table, p. 1623 - 1626 (2010/09/05)
Three new α-cyclopropyl nitrones have been synthesized as mechanistic probes for reductive cross-coupling reactions of nitrones. The α-cyclopropylcarbinyl radical intermediate formed by single electron transfer from SmI2 to these nitrones is no
Concerning the reactivity of ptad with isomeric dienes: The mechanism of the Diels-Alder cycloaddition
Alberti, Mariza N.,Orfanopoulos, Michael
supporting information; experimental part, p. 1659 - 1662 (2009/09/07)
Cyclopropyl substituted dienes are employed as mechanistic probes in the triazolinedione Diels-Alder (DA) reaction. In aprotic and protic solvents, apart from the DA adducts that bear an intact cyclopropyl group, complicated and rearranged products are also obtained. These results provide solid evidence for the involvement of an open intermediate with a lifetime greater than 2 x 10 -12 s.
Facile and efficient way to synthesize the radical cyclization precursor methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3-oxo-2- (phenylseleno)propanoate for kinetic research
Yu, Jindi,Lian, Gaoyan,Zhang, Danwei
, p. 37 - 46 (2007/10/03)
Methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3- oxo-2-(phenylseleno)propanoate was prepared in 10 steps in good to excellent yield using benzophenone and hydrazine hydrate as the starting materials. Copyright Taylor & Francis Group, LLC.
Thermal C2-C6 cyclization of enyne-allenes. Experimental evidence for a stepwise mechanism and for an unusual thermal silyl shift
Schmittel, Michael,Mahajan, Atul A.,Bucher, Goetz,Bats, Jan W.
, p. 2166 - 2173 (2007/10/03)
Enyne-allenes 4a-c bearing various cyclopropyl systems as radical clock reporter groups at the allene terminus have been synthesized and subjected to thermal C2-C6 cyclization. The ratio of ene versus formal Diels-Alder products could be rationalized on the basis of steric effects. Only the thermolysis of 4c, equipped with the fast diphenylcyclopropylcarbinyl radical clock, afforded a 1,3-butadienyl benzofulvene clearly formed via cyclopropyl ring opening. This finding provides unambiguous evidence for a stepwise mechanism of the C2-C6 cyclization making it possible to suggest a lifetime for the intermediate diradical of > 1 × 10-10 s (at 170 °C). An interesting corollary was the isolation of an unexpected silyl shift product in the thermolysis of all three enyne-allenes that allows explanation of the loss of the TIPS group in some of the Diels-Alder products. For a full understanding of the mechanism, silyl and hydrogen shift processes were interrogated using DFT.
Stereocontrol of intramolecular Diels-Alder reactions by an allylic diphenylcyclopropyl group
Tripoli, Regis,Cayzer, Tory N.,Willis, Anthony C.,Sherburn, Michael S.,Paddon-Row, Michael N.
, p. 2606 - 2616 (2008/03/12)
Intramolecular Diels-Alder reactions of ester-linked 1,3,8-nonatrienes carrying a diphenylcyclopropyl substituent attached to C1 proceed with high levels of stereoselectivity. The stereochemical outcomes of these reactions are explained by reference to B3
