4733-52-2Relevant articles and documents
Dearomatization Reactions Using Phthaloyl Peroxide
Eliasen, Anders M.,Christy, Mitchell,Claussen, Karin R.,Besandre, Ronald,Thedford, Randal P.,Siegel, Dionicio
, p. 4420 - 4423 (2015)
A new oxidative dearomatization reaction has been developed using phthaloyl peroxide to chemoselectively install two oxygen-carbon bonds into aromatic precursors. The oxidation reaction proceeds only once; addition of superstoichiometric equivalents of ph
Energy Read-out as a Probe of Kinetically Hidden Transition States
Alvi, Scheherzad,Singleton, Daniel A
supporting information, p. 2174 - 2177 (2021/04/05)
The initial energy in a reactive intermediate is derived from the transition state before the intermediate but can affect selectivity after the intermediate. In this way an observable selectivity can report on a prior, kinetically hidden mechanistic step. This new type of mechanistic probe is demonstrated here for the oxidation of 1-methylcyclobutanol by phthaloyl peroxide/Bu4N+Br-, and it supports a hypobromite chain mechanism in place of the previously proposed hydrogen atom transfer mechanism.
Pentamethylphenyl (Ph*) and Related Derivatives as Useful Acyl Protecting Groups for Organic Synthesis: A Preliminary Study
Cheong, Choon Boon,Frost, James R.,Donohoe, Timothy J.
supporting information, p. 1828 - 1832 (2020/10/06)
A study of acyl protecting groups derived from the Ph? motif is reported. While initial studies indicated that a variety of functional groups were not compatible with the Br 2-mediated cleavage conditions required to release the Ph? group, strategies involving the use of different reagents or a modification of Ph? itself (Ph*OH) were investigated to solve this problem.
Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
supporting information, p. 2647 - 2654 (2017/04/03)
Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.
Cycloadditions of azides with arynes via photolysis of phthaloyl peroxide derivatives
Chang, Denghu,Zhu, Dan,Shi, Lei
, p. 5928 - 5933 (2015/06/16)
Photolysis of phthaloyl peroxides yields arynes, which undergo [3 + 2] cycloadditions with azides. This reaction tolerates a variety of organic azides and phthaloyl peroxides and affords the corresponding benzotriazoles in moderate to good yields at room
A protocol to generate phthaloyl peroxide in flow for the hydroxylation of arenes
Eliasen, Anders M.,Thedford, Randal P.,Claussen, Karin R.,Yuan, Changxia,Siegel, Dionicio
supporting information, p. 3628 - 3631 (2014/08/05)
A flow protocol for the generation of phthaloyl peroxide has been developed. This process directly yields phthaloyl peroxide in high purity (>95%) and can be used to bypass the need to isolate and recrystallize phthaloyl peroxide, improving upon earlier batch procedures. The flow protocol for the formation of phthaloyl peroxide can be combined with arene hydroxylation reactions and provides a method for the consumption of peroxide as it is generated to minimize the accumulation of large quantities of peroxide.
Synthesis and reaction of phthaloyl peroxide derivatives, potential organocatalysts for the stereospecific dihydroxylation of alkenes
Yuan, Changxia,Axelrod, Abram,Varela, Michael,Danysh, Laura,Siegel, Dionicio
supporting information; experimental part, p. 2540 - 2542 (2011/06/21)
To improve the synthesis and reactivity of phthaloyl peroxide derivatives a method has been developed using sodium percarbonate and phthaloyl chlorides. The reactions of the new phthaloyl peroxide derivatives with trans-stillbene as well as the improved reactivity of 3,4-dichlorophthaloyl peroxide with a variety of alkenes are reported.
Photolysis of indan-l,2-dione derivatives in oxygen-doped argon matrix at low temperature
Itoh, Takayoshi,Tatsugi, Jiro,Tomioka, Hideo
body text, p. 475 - 481 (2009/08/07)
Photolysis of indan-l,2,3-trion (la), benzo[ft]furan-2,3-dione (lb), and N-methylisatin (1c) in argon matrix either with or without oxygen at 10 K was investigated by IR spectroscopy in combination with DFT calculations. The results indicate that while 1a and 1b gave the products mixture as a result of α-cleavage, followed by decarbonylation, 1c was rather photostable under similar conditions. However, when the irradiation was carried out in argon matrix doped with 20% oxygen, 1c decomposed much more efficiently than that in argon matrix and cyclic diacyl peroxide presumably formed by trapping of initial diradical originating from α-cleavage by molecular oxygen was detected. Similar irradiation of 1b also gave cyclic diacyl peroxide along with photodecarbonylation products, but irradiation of 1a in oxygen-doped matrix produced not only cyclic diacyl peroxide but also products as a result of oxidation of photodecarbonylation product. The present observation reveals that photolysis of ketones in oxygen-doped matrix at low temperature provides useful information concerning the reactivities of ketones toward α-cleavage.
