78386-38-6

Upstream product

• 96-09-3 styrene oxide 
• 507-20-0 tertiary butyl chloride 
• 51558-95-3 1-phenyl-2-(phenylselanyl)ethanol 
• 591-50-4 iodobenzene 
• 926-02-3 tert-butyl vinyl ether 
• 774-65-2 benzoic acid tert-butyl ester 
• 100-42-5 styrene 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 115525-20-7 (1-tert-Butoxy-2,2-dichloro-cyclopropyl)-benzene 
• 942-92-7 caprophenone 
• 31366-07-1 3,3-dimethyl-1-phenyl-butan-1-one 
• 124286-43-7 diethyl 2-methyl-2-(2-oxo-2-phenylethyl)malonate 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 94011-49-1 diethyl phenacylmalonate 
• 150013-93-7 3-(2-oxo-2-phenylethyl)dihydrofuran-2(3H)-one 
• 6938-44-9 ethyl 2-methyl-4-oxo-4-phenyl-butanoate 
• 23033-63-8 3-methyl-1-phenyl-1-pentanone 
• 594815-53-9 ethyl 2,2-dimethyl-4-oxo-4-phenylbutanoate 
• 777882-71-0 (1R,3R,4R)-1,7,7-Trimethyl-3-(2-oxo-2-phenyl-ethyl)-bicyclo[2.2.1]heptan-2-one 
• 777882-71-0 (1R,3S,4R)-1,7,7-Trimethyl-3-(2-oxo-2-phenyl-ethyl)-bicyclo[2.2.1]heptan-2-one 
• 65885-28-1 1-phenyl-3-(phenylsulfonyl)propan-1-one 
• 777882-57-2 1-adamantan-1-yl-4-phenylbutane-1,4-dione 

Relevant academic research and scientific papers

A facile solid-phase synthesis of vinyl ethers using a selenium traceless linker

A simple, efficient and environmentally friendly procedure for the solid-phase synthesis of vinyl ethers in good yields and purities by reaction of polystyrene-supported 2-hydroxyalkyl selenide with primary or secondary organic halides and subsequent oxid

Convenient one-pot synthesis of vinyl ethers from phenyl 2-hydroxyalkyl selenides

Vinyl ethers were prepared with good yields in a one-pot, two-step transformation by O-alkylation reaction of phenyl 2-hydroxyalkyl selenides with primary or secondary organic halides followed by oxidation elimination with 30% hydrogen peroxide. Copyright

Carbon-carbon bond formation by radical addition-fragmentation reactions of O-alkylated enols

α-tert-Butoxystyrene [H2C = C(OBut)Ph] reacts with α-bromocarbonyl or α-bromosulfonyl compounds [R 1R2C(Br)EWG; EWG = -C(O)X or -S(O2)X] to bring about replacement of the bromine atom by the phenacyl group and give R 1R2C(EWG)CH2C(O)Ph. These reactions take place in refluxing benzene or cyclohexane with dilauroyl peroxide or azobis(isobutyronitrile) as initiator and proceed by a radical-chain mechanism that involves addition of the relatively electrophilic radical R 1R2(EWG)C* to the styrene. This is followed by β-scission of the derived α-tert-butoxybenzylic adduct radical to give But*, which then abstracts bromine from the organic halide to complete the chain. α-1-Adamantoxystyrene reacts similarly with R 1R2C(Br)EWG, at higher temperature in refluxing octane using dα-tert-amyl peroxide as initiator, and gives phenacylation products in generally higher yields than are obtained using α-tert-butoxystyrene. Simple iodoalkanes, which afford relatively nucleophilic alkyl radicals, can also be successfully phenacylated using α-1-adamantoxystyrene. O-Alkyl O-(tert-butyldimethylsilyl) ketene acetals H2C=C(OR)OTBS, in which R is a secondary or tertiary alkyl group, react in an analogous fashion with organic halides of the type R1R2C(Br)EWG to give the carboxymethylation products R1R2C(EWG)CH 2CO2Me, after conversion of the first-formed silyl ester to the corresponding methyl ester. The silyl ketene acetals also undergo radical-chain reactions with electron-poor alkenes to bring about alkylation-carboxymethylation of the latter. For example, phenyl vinyl sulfone reacts with H2C=C(OBut)OTBS to afford Bu tCH2CH(SO2Ph)CH2CO2Me via an initial silyl ester. In a more complex chain reaction, involving rapid ring opening of the cyclopropyldimethylcarbinyl radical, the ketene acetal H 2C=C(OCMe2C3H5-cyclo)OTBS reacts with two molecules of N-methyl- or N-phenyl-maleimide to bring about [3 + 2] annulation of one molecule of the maleimide, and then to link the bicyclic moiety thus formed to the second molecule of the maleimide via an alkylation-carboxymethylation reaction.

A new efficient tetraphosphine/palladium catalyst for the Heck reaction of aryl halides with styrene or vinylether derivatives

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system efficiently catalyses the Heck reaction of aryl halides with styrene and vinylether derivatives. High turnover numbers can be obtained for the reaction of several aryl halides with styrene and styrene derivatives. Lower turnover numbers have been observed in the presence of vinylethers.

REACTIVITY OF THE DOUBLE BOND IN ALKOXY- AND HALOGEN-SUBSTITUTED STYRENES TOWARD DICHLOROCARBENE

The relative rate constants for the reactions of dichlorocarbene with a series of alkoxy- and halogen-substituted styrenes were determined.It was established that these values correlate with the difference between the energies of the HOMO of styrene and t

Carbonyl Methylenation Using a Titanium- Aluminum (Tebbe) Complex

The titanium-aluminum (Tebbe) complex is shown to be an effective methylenating agent for a variety of carbonyl groups.The reaction is unique in that the carbonyl groups of carboxylic acid derivatives are readily methylenated.Thus vinyl enol ethers are prepared from esters and enamines are formed from amides.The complex provides a method for methylenating hindered or base sensitive ketones that is advantageous to the Wittig reagent.Selective methylenation of dicarbonyl compounds is also accomplished.