79629-42-8

Upstream product

• 100-67-4 potassium phenolate 
• 513-31-5 2-bromoallyl bromide 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 96-11-7 1,2,3-tribromopropane 
• 1746-13-0 allyl phenyl ether 

Downstream Products

• 99029-95-5 2,3-bis(phenoxymethyl)buta-1,3-diene 
• 1746-13-0 allyl phenyl ether 
• 244056-20-0 1,1,2-tribromo-2-phenoxymethylcyclopropane 
• 36963-72-1 (3-phenoxyprop-1-en-2-yl)benzene 
• 199923-53-0 1,2-diphenoxy-2-propene 
• 1236063-70-9 (5,5-dimethyl-2-methylenehex-3-ynyloxy)benzene 
• 1236063-69-6 (2-methylenenon-3-ynyloxy)benzene 
• 133846-59-0 (E)-3-phenoxy-1-phenylsulphinylprop-1-ene 
• 133846-33-0 (Z)-3-phenoxy-1-phenylsulphinylprop-1-ene 
• 18229-83-9 (4,4-diethoxybut-2-ynyloxy)benzene 
• 83338-55-0 2-Phenoxymethyl-2-phenyl-oxirane 
• 13610-02-1 1-phenoxy-2-propyne 
• 874194-31-7 2-(2-bromo-allyl)-phenol 

Relevant academic research and scientific papers

Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N?H and Aryl C?H Bond Cleavage

An asymmetric palladium-catalyzed intramolecular oxidative aminoarylation of alkenes has been developed with quinoline–oxazoline chiral ligands and Ag2CO3 as the oxidant. Various indolines containing a quaternary stereogenic center were synthesized in high yield with excellent enantioselectivity. Preliminary mechanistic studies suggest that the addition of a catalytic amount of phenylglyoxylic acid significantly accelerates the reaction and slightly enhances the enantioselectivity.

One-pot method for regioselective bromination and sequential carbon-carbon bond-forming reactions of allylic alcohol derivatives

An efficient one-pot method for the regioselective bromination of allylic alcohol derivatives (two-step reaction sequence) followed by Sonogashira, Negishi, or Suzuki-Miyaura coupling reactions in the same reaction vessel (three-step reaction sequence) ha

1,8-diazabicyclo[5.4.0]undec-7-ene-promoted regioselective elimination of vicinal dibromides having an adjacent O-and/or N-functional group

We have investigated the DBU-promoted HBr-elimination of vicinal dibromides having an adjacent O- and/or N-functional group under mild basic conditions. The elimination of 1-oxygenfunctionalized 2,3-dibromopropanes was more regioselective than that of 1-n

TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group

Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.

Synthesis of excitatory amino acid analogues

A general route to excitatory amino acid analogues has been developed as exemplified by the synthesis of A-1 and A-2. The key reactions involved were a Negishi coupling of Jackson's organozinc reagent with vinyl bromide 8 and subsequent ring closure of 15

Controlling chemoselectivity in vinyl and allylic C-X bond activation with palladium catalysis: A pKa-based electronic switch

It has been demonstrated that the same Pd catalyst can be used to effect allylic substitution or vinylic cross-coupling reactions selectively and interchangeably on polyfunctionalized olefin building blocks despite the differences in reaction mechanism. T

The synthesis of ethanolamine libraries from olefin scaffolds

A solution-phase, multi-reaction sequence has been developed for the parallel synthesis of ethanolamine libraries. This approach uses 2,3-dibromopropene as a template for the synthesis of a small olefin sub-library, which is then further functionalized to

Neighbouring-group influence on the ring opening of 2-aryloxymethyl-1,1,2-tribromocyclopropanes under phase-transfer conditions

When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.

Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals.Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(?-exo)exo, 6-(?-endo)exo, and 6-(?-exo)exo mode, respectively.Radical 7 undergoes competitive 1,5-hydrogen translocation.Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively.Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent β-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation.Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization).Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group.Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. α-Oxy(and α-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.