29689-80-3

Upstream product

• 50555-61-8 3,3-dimethyl-1,2-diphenyl-1-cyclopropene 
• 53546-25-1 1,2-Diphenyl-3-methyl-2-buten-1-ol 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 62-53-3 aniline 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 100-52-7 benzaldehyde 
• 26524-38-9 α-chloro-β,β-dimethylstyrene 
• 27962-40-9 2-hydroxy-3-methyl-1,2-diphenylbutan-1-one 
• 86108-35-2 Toluene-4-sulfonic acid 2,2-dimethyl-3-oxo-1,3-diphenyl-propyl ester 

Downstream Products

• 82323-78-2 1,2-diphenyl-3-methyl-2-buten-1-one tosylhydrazone 
• 50555-62-9 1,2-diphenyl-3-methyl-1-diazo-2-butene 

Relevant academic research and scientific papers

Photosensitizer-Free Visible-Light-Mediated Gold-Catalyzed 1,2-Difunctionalization of Alkynes

Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional-group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one-pot processes. With a P,N-bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex.

Clemmensen reduction. XII The synthesis and acidolysis of some diaryl-substituted cyclopropane-1,2-diols. The possible involvement of a cyclopropyl cation

The generation of a number of 1,2-diarylcyclopropane-1,2-diols is reported. Reaction of these in situ with acid gives, primarily, an α,β-unsaturated ketone in which the aryl substituent attached to the double bond is that which is best able to stabilize a benzylic cation. It is proposed that the reaction proceeds by O-protonation of the cyclopropane- 1,2-diol, followed by loss of water and opening of the resulting cyclopropyl cation and final deprotonation. Such initial O-protonation contrasts with the C-protonation normally observed in the acidolysis of cyclopropanols and other dialkyl- and alkylaryl-cyclopropane-1,2-diols.

AN INTERPRETATION OF THE SUBSTITUENT EFFECT IN THE BLAISE REARRANGEMENT IN TERMS OF PI-ORBITALS

The migratory aptitude of the substituent groups in the Blaise rearrangement can be explained in terms of the pi-electronic properties of the groups in the highest occupied molecular orbitals.The rates of the rearrangement reaction with relation to the substituent groups were also rationally understood based on the energy levels of the molecular orbitals.

THE ROLE OF CYCLIC PEROXIDES IN THE REACTIONS OF 1,2-DIPHENYLCYCLOPROPENES AND CYCLOBUTENES WITH SINGLET OXYGEN (1a,b,c,2)

An array of cyclic peroxy intermediates, including dioxetanes, endoperoxides and 1,2-dioxoles, are advanced as intermediates in the reactions of 1O2 with 1,2-diphenylcyclopropenes and cyclobutenes.