2491-41-0

Upstream product

• 1450-63-1 1,1,4,4-tetraphenyl-1,3-butadiene 
• 141-97-9 ethyl acetoacetate 
• 108-86-1 bromobenzene 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 495-40-9 propiophenone 
• 591-51-5 phenyllithium 
• 1483-74-5 1,1,4,4-tetraphenyl-2-butyne-1,4-diol 
• 63469-15-8 1,1,4,4-tetraphenyl-1,4-butanediol 
• 98760-59-9 2,2-diphenyl-3-(2,2-diphenylvinyl)oxirane 
• 118745-75-8 3,3,7,7-Tetraphenyl-7H-[1,2,4]trioxepine 
• 59856-52-9 trans-1,1,4,4-tetraphenyl-2-butene-1,4-diol 

Downstream Products

• 2491-42-1 1.1.3.4-Tetraphenyl-buten-⁽¹⁾-ol-⁽⁴⁾ 

Relevant academic research and scientific papers

Fe(II)-mediated fragmentation of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes through competitive single electron transfer pathway and Lewis acid pathway

Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) with FeBr2 in THF afforded 1,4-diarylbutan-1,4-diones 2a-d and 1,4-diaryl-7-oxabicyclo[2.2.1]heptanes 3a-d. On the other hand, 4-aryl-3-cyclohexenones 4c-d and p-substituted phenols 5c-d were obtained in the reactions of 1c-d with FeBr2 in CH2Cl2. A new fragmentation mechanism involving an electrophilic oxyl radical 1,5-substitution and a nucleophilic O-1,2-aryl shift is proposed based on the product analysis. In addition, the in vitro antimalarial activities of 1a-d were tested.

Multiple arylation of alkyl aryl ketones and α,β-unsaturated carbonyl compounds via palladium catalysis

Alkyl (ethyl to butyl) aryl ketones have been found to undergo multiple arylation on the alkyl chains accompanied by oxidative unsaturation upon treatment with excess aryl bromides in the presence of a palladium catalyst and a base. In the case of phenyl propyl ketones, for example, the arylation occurs up to five times on the α-and γ-positions as well as the ortho-position of the phenyl ring to give 1-(biphenyl-2-yl)-2,4,4,4-tetraphenyl-2-buten-1-ones along with other arylation products. A number of α,β-unsaturated carbonyl compounds are also arylated multiply on the α- and γ-positions.

Formation of 1,2,4-trioxolanes via 9,10-dicyanoanthracene(DCA)-sensitized photo-oxygenation of 2,2-diaryl-3-(2,2-diarylvinyl)oxiranes

9,10-Dicyanoanthracene-sensitized photo-oxygenation of 2,2-diaryl-3-(2,2-diarylvinyl)oxiranes 3 in acetonitrile did not afford the corresponding 1,2,4-trioxepines 4, but 1,2,4-trioxolanes 7. The structural assignment of 7 was reported, and the mechanism of the formation of 7 was proposed.

Manganese(III) or Cobalt(III)-Mediated Oxidative Radical Reactions of Terminal Dienes. One-Pot Synthesis of Bis(dihydrofuran)s

The reactions of terminal dienes such as 1,4-pentadienes and 1,5-hexadienes with tris(2,4-pentanedionato)manganese(III) () gave α,ω-bis(dihydrofuryl)alkanes (abbreviated bis(dihydrofuran)s, hereafter) in good yields.The reactions with tris(2,4-pentanedionato)cobalt(III) () instead of yielded the same bis(dihydrofuran)s quantitatively.The dienes also reacted with ethyl 3-oxobutanoate in the presence of manganese(III) acetate () or cobalt(III) acetate () to produce the corresponding bis(dihydrofuran)s.The reactions of 1,3-butadienes with the manganese(III) or cobalt(III) complexes afforded only mono(dihydrofuran)s and oxidative rearrangement products, but the corresponding bis(dihydrofuran)s were not formed.The reaction of 1,5-hexadienes with ethyl hydrogen malonate in the presence of did not give bis-annulated products, but mono(γ-lactone)s in moderate yields.The synthetic applications and limitations of the bis(dihydrofuran)s formation are discussed.

Formation of 1,2,4-Trioxepines via 9,10-Dicyanoanthracene(DCA)-sensitized Photo-oxidation of Arylvinyloxiranes

9,10-Dicyanoanthracene-sensitized photo-oxidation of arylvinyloxiranes in acetonitrile affords the corresponding 1,2,4-trioxepines.

The Photochemistry of Bis(2,2-diphenylvinyl) Ether: A Search for the 3-Oxa-di-?-methane Rearrangement

A convenient synthesis for bis(2,2-diphenylvinyl) ether (1a) from diglycolic acid via dehydration of 2,2'-oxybis(1,1-diphenylethanol) (3a) is described.The solution photochemistry of divinyl ether 1a derives from its singlet ?,?*-state and parallels that of the unsubstituted divinyl ether (1d) and that of furan in the gas phase.Formation of a singlet D?,? vinyl-vinyloxy radical pair is the primary photoreaction (Φ-S = 0.12-0.19).All photoproducts can be convincingly rationalized from this initial radical pair.For example, cage recombination affords 2,2,4,4-tetraphenyl-3-butenal (13) as the main product.The mechanistic interpretations are based on results from product studies, photo-CIDNP and crossover experiments.The triplet excited state of divinyl ether 1a was found to be inert toward decomposition. trans,trans-Bis(2-phenylvinyl) ether (1c) could be prepared from trans,trans-1,4-diphenyl-1,3-butadiene via epoxidation of its Diels-Alder adduct with bis(2,2,2-trichloroethyl)azodicarboxylate and thermal denitrogenation of the corresponding azo compound.The divinyl ether 1c readily cis-trans isomerizes upon triplet sensitization, thus implicating cis-trans isomerization as the deactivation mode of triplet divinyl ether 1a. 3-Oxa-di-?-methane reactivity of divinyl ether 1a could not be observed.This result is interpreted in terms of Zimmerman's formalism of bond-order control.Irradiation of the authentic vinyloxirane 7 resulted in the photoextrusion of diphenylcarbene affording 3,3-diphenylpropenal.The intermediacy of the corresponding carbonyl ylide 14 was established by low-temperature UV spectroscopy.

The Pyrolyses of 1,1,4,4-Tetraphenyl-1,4-butanediol and 1,1,4,4-Tetraphenyl-2-butene-1,4-diol Derivatives. Decomposition Reactions to Form Olefins via the Elimination of Two Mole Equivalents of the Hydroxydiphenylmethyl Radical

The pyrolysis of 1,1,2,4,4-pentaphenyl-1,4-butandiol, trans-1,2-bis(hydroxydiphenylmethyl)hexane, trans-1,2-bis(hydroxydiphenylmethyl)indan, and cis-endo- and trans-1,2-bis(hydroxydiphenylmethyl)bicycloheptane gave styrene, cyclohexene, indene, and norbornene respectively, accompanied by benzophenone and benzhydrol.The pyrolysis of trans-1,2-bis(hydroxydiphenylmethyl)spironona-4,6,8-triene afforded indene via rearrangement to form trans-1,2-bis(hydroxydiphenylmethyl)indan.The pyrolysis of cis-1,1,4,4-tetraphenyl-2-butene-1,4-diol afforded 2,2,5,5-tetraphenyl-2,5-dihydrofuran.On the other hand, trans-1,1,4,4-tetraphenyl-2- butene-1,4-diol afforded 1,2,4,4-tetraphenyl-3-buten-1-one.The mechanisms of these decomposition reactions are discussed.