34966-91-1

Upstream product

• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 611-70-1 phenyl isopropyl ketone 

Downstream Products

• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 200395-89-7 dibromo di-n-hexyl tellurium(IV) 
• 41231-85-0 2,3-Diphenyl-4-methyl-3-penten-2-ol 
• 477706-42-6 2,3,3,4,4,5,5-heptafluoro-1-(2-methyl-1-phenyl-1-propenyl)cyclopentene 
• 5912-93-6 1-bromo-2-methyl-1-phenyl-1-propene 

Relevant academic research and scientific papers

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation can be done under enantioselective conditions are reported.

Synthesis of novel thermally reversible photochromic spiro[adamantane-2,7′(6′H)-benzothiophene]

A new thermally reversible photochromic compound, 4′,5′-hexafluoropropano-6′-phenylspiro[adamantane-2, 7′(6′H)-benzothiophene], derived from UV-irradiation of 2-(1-adamantylidene-1-phenylmethyl)-3,3,4,4,5,5-hexafluoro-1- (3-thienyl)cyclopentene via the ph

Debrominations of vic-Dibromides with Diorganotellurides. 1. Stereoselectivity, Relative Rates, and Mechanistic Implications

Debrominations of vic-dibromides with diaryl tellurides 1-4 and di-n-hexyl telluride (9) are described. A mechanistic explanation of the debromination is offered which accounts for several key experimental observations: (1) the reaction is highly stereoselective with erythro-dibromides giving trans-olefins and threo-dibromides giving cis-olefins, (2) the reaction is accelerated by more electron-rich diorganotellurides, (3) the reaction is accelerated in a more polar solvent, (4) the reaction is accelerated by the addition of carbocation-stabilizing substituents to the carbons bearing the bromo substituents, and (5) erythro-dibromides are much more reactive than threo-dibromides. It is proposed that bromonium ion formation from the vic-dibromide is slow and rate-determining. Bromonium ion formation is followed by rapid scavenging of "Br-" by the diorganotelluride. The bromonium ion formation provides stereoselectivity and eclipsing interactions lower the reactivity of threo-dibromides. No intermediate species were observed by 1H NMR.

Competition of Mechanisms in Nucleophilic Substitution of Vinyl Halides. An Unequivocal Example of the Vinylic SRN1 Route

In a search for an unambiguous example of the vinylic SRN1 route, several vinyl bromides and iodides were reacted mostly with (-)CH2COCMe3, and sometimes with (-)CH2COPh, (-)CH(Me)COEt, and (EtO)2PO(-) ions, under Fe(2+)- or photostimulation in Me2SO.Vinyl halides having vinylic hydrogens, such as β-bromostyrene, gave acetylenic products, e.g., phenylacetylene or a tertiary PhCC-substituted alcohol, whereas vinyl halides with allylic hydrogens, such as Me2C=C(I)CHMe2, gave a substituted allene.Reduction products of the halogen, as well as substitution and rearranged substitution products, were also formed.The operation of ionic elimination-addition routes accounts for formation of most of the products, while the reduction products arise from an intermediate vinyl radical.Ph2C=C(Br)Ph (20) and Me2C=C(Br)Ph (25) gave both substitution and reduction products, but Me2C=C(Br)-t-Bu (23) gave only a reduction product.Formation of substitution products from the conjugated 20 and 25 was ascribed to a reaction via a vinylic SRN1 route, while lack of substitution in 23 is related to its nonconjugated system and to the consequent higher energy that the radical anion of the substitution product would have.The one here reported seems to be the first case of an exclusive genuine vinylic SRN1 process.

TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFECTIVE SOURCE OF FLUORIDE ION FOR HALOFLUORINATION OF ALKENES

Vicinal halofluorides have been prepared from the corresponding alkenes by reaction with a stoichiometric amount of Bu4N+H2F3- as a source of fluoride anion and an excess of an N-halosuccinimide (NXS).The reaction products are obtained in good yields, with a prevalent Markownikoff regiochemistry.Olefins containing hydroxy, epoxy, acetoxy and alkoxy groups do not undergo side reactions under these reaction conditions.

The α-Vinylation of β-Dicarbonyl Compounds by Alk-1-enyl-lead Triacetates

Treatment of (E,E)-distyrylmercury (1) with lead tetra-acetate gave a mixture of (E)-styrylmercury acetate (3) and (E)-styryl-lead triacetate (2), which decomposed to (E)-styryl acetate (4) and lead(II) acetate.The vinyl-lead compound (2), generated in this way, reacted rapidly with β-keto ester (5) to give the α-(E)-styryl derivative (6) in synthetically useful yield.This procedure for the α-vinylation of (5) has been applied to the divinylmercury compounds (7)-(13), and to the synthesis of the α-(E)-styryl β-dicarbonyl compounds (28), (30), (32), and (34).Compounds (6), (28), (30), (32), and (34).Compounds (6), (28), (30), (32), and (34) have also been produced by reaction with lead compound (2) generated by reaction of tributyl-(E)-styrylstannane (36) and lead tetra-acetate.Isolation of the relatively stable cyclopent-1-enyl-lead triacetate (21b), and its reaction with keto ester (5) to give a quantitative yield of compound (18), provided evidence that vinyl-lead triacetates are the vinylating species.