155694-19-2

Upstream product

• 882-59-7 1,1-diphenyloxirane 
• 530-48-3 1,1-Diphenylethylene 

Downstream Products

• 29539-01-3 2-azido-1,1-diphenylethylene 
• 86-29-3 Diphenylacetonitrile 
• 25084-02-0 2,2-diphenyl-2H-azirine 
• 1504-16-1 3-phenyl-1H-indole 
• 4382-96-1 2-amino-1,1-diphenylethanol 

Relevant academic research and scientific papers

Preparation method of beta-azide alcohol compound

The invention discloses a preparation method of a beta-azide alcohol compound. According to the method, an olefin compound shown in a formula I, an azide source shown in a formula II and a photocatalyst are mixed in a non-nucleophilic organic solvent; and

Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes

A highly efficient visible-light-promoted metal-free aerobic hydroxyazidation of alkenes has been developed. This protocol was operationally simple with broad substrate scope using relatively simple and readily available starting materials, such as alkene

Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols

(Chemical Equation Presented). An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.

The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)-cyanomethylamines. Part 2. Mechanism

The mechanism of the rearrangement of N-(1-arylalkylidene)cyanomethylamines ArC(=NCH2CN)R 1 to the corresponding nitriles ArCH(CN)R2 (in DMF, at 150°C, with K2CO3) is described. Reaction 1 → 2 was investigated for different types of imine 1, and it was found that with a leaving group other than CN- the reaction does not proceed to yield the nitrile, whereas imines such as PhC(=NCH2CN)H, prepared starting from aldehydes rather than ketones, yield the expected phenylacetonitrile even at temperatures as low as 120°C. Evidence for the mechanism comes from a study of the reactivity of the postulated intermediates: 2-cyano-3-phenylaziridine 4c, and 2,2-diphenyl-2H-azirine 5b. The route involving aziridine 4c is ruled out, since this compound does not react at all under the investigated conditions. The 2H-azirine 5b instead, yields the corresponding diphenylacetonitrile in DMF with K2CO3, at 150°C. The transformation seems to involve an initial deprotonation, followed by an intramolecular ring closure-CN elimination step, which yields the 2H-azirine. The azirine then isomerizes to the nitrile. Additional evidence for the intermediacy of the 2H-azirine, based on 1H NMR monitoring of the reaction 1 → 2, is described. Finally, the results of a simple isotope exchange experiment provide a rationale for the previously observed scrambling of labels, and further confirm the proposed mechanism.

The oxidation of methylene carbon-carbon double bonds under Fe(III)-TBHP and Fe(III)-TBHP-PA conditions

The oxidation of 1,1-diphenylethylene under Fe(III)-TBHP and Fe(III)-TBHP-Pa conditions followed a pathway alkene to intermediate A to intermediate B to ketone. Intermediate A could be trapped by NaN3.