28164-58-1

Upstream product

• 129589-46-4 2-acetyl-1-allyloxynaphthalene 
• 26074-52-2 2-bromo-butyryl bromide 
• 90-15-3 α-naphthol 
• 106-95-6 allyl bromide 
• 20009-25-0 allyl naphthyl ether 

Downstream Products

• 1143446-24-5 C₂₃H₂₀O₃ 
• 1143446-27-8 C₂₃H₂₀O₃ 
• 1207446-45-4 C₁₉H₁₅BrO₃S 
• 63972-43-0 2-((1-(benzyloxy)naphthalen-2-yl)methyl)oxirane 
• 63972-42-9 2-allyl-1-(benzyloxy)naphthalene 

Relevant academic research and scientific papers

Bismuth triflate catalyzed Claisen rearrangement of allyl naphthyl ethers

Bismuth triflate was found to be an efficient catalyst for the Claisen rearrangement of allyl naphthyl ethers. The reaction proceeds smoothly with a catalytic amount of bismuth triflate (20 mol %) to afford the corresponding ortho-allyl naphthol in moderate to good yields in most cases.

Alternative Lewis acids to effect Claisen rearrangement

Yb(OTf)3 and DIBAL-H are developed as alternative Lewis acids for effecting Claisen rearrangement of allyl, crotyl and prenyl aryl ethers.

Solid composite copper-copper chloride assisted alkylation of naphthols promoted by microwave irradiation

Naphthyl ethers and naphthyl esters were synthesized in good yield by using mixture of copper metal powder and copper (II) chloride in conventional microwave oven in short time.

Claisen rearrangement of allyl ethers of isomeric acetylnaphthols under catalytic conditions

Claisen rearrangement of the isomeric allyl ethers (1 and 6) of 2-acetyl-1-naphthol and 1-acetyl-2-naphthol has been studied using a Bronsted or protic acid (CF3COOH) and aprotic or Lewis acids as catalysts.The rearrangement of 1 in TFA gives 2-acetyl-1--naphthol (2), 1-acetoxy-2-allylnaphthalene (3) and 2-allyl-1-naphthol (4), but in BF3*OEt2 it resulted in only 4.However, Claisen rearrangement of 1 under Pd(II) mediation furnishes 2-acetyl-4-allyl-1-naphthol (5) and 4.The isomeric ether 6 rearranges in TFA to give 1-allyl-2-naphthol(7) and 2-acetoxy-1-allylnaphthalene (8) while resists rearrangement with BF3*OEt2.However, with Pd(II) it undergoes isomerisation of allyloxy double bond furnishing 1-acetyl-2-(cis-enyloxy)naphthalene (9).All the products have been characterised by their elemental analyses and spectral data (IR, UV, PMR, and mass) and their formation has been rationalised.

Photolyses of (3-Naphthoxypropyl)-, (4-Naphthylbutyl)-, and (4-Naphthyl-4-oxobutyl)cobaloxime

The cobalt-carbon bond of the titled compounds is photochemically cleaved to generate an organoradical and a cobaloxime(II) radical pair. 3-(1- or 2-naphtoxy)propyl, 4-(1- or 2-naphthyl)butyl, and 4-(1-or 2-napthyl)-4-oxobutyl radicals thus formed undergo three types of reactions: (a) hydrogen abstraction to give a saturated terminal, (b) hydrogen elimination to give a terminal olefin, and (c) substitution on the naphthalene ring.In benzene and radicals follow process b exclusively (the radicals from (3-(2-napthoxy)propyl)cobaloxime (1a), (3-(1-napthoxy)propyl)cobaloxime (2a), and (4-(1-napthyl)butyl)cobaloxime (2 b)) or preferentially (the radicals from (4-(2-napthyl)butyl)cobaloxime (1 b), (4-(2-napthyl)-4-oxobutyl)cobaloxime (1c), and 4-(1-napthyl)-4-oxobutyl)cobaloxime (2c)).In chloroform, process a becomes important to the extent as the sum of the other two processes.In water-acetonitril (4:1), process c becomes important and even takes precedence of others for the radicals from 1b and 1c.This feature is accounted for by the folding of the side chain of hydrophobic radicals.Encapsulation of the radicals in β-cyclodextrin stimulates process c except for the case of the radical from 2c.In the case of cobaloxime 2c, α-cyclodextrin does not effect the partition process of the intermediate radical.This feature is accounted for by the shallow inclusion of the radical due to the hydrogen bonding as depicted in Figure 1d.