573-57-9

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 1599, 1965 DOI: 10.1139/v65-211Chemistry Letters, 12, p. 1211, 1983

Purification Methods

Dissolve it in Et2O, wash it with H2O, dry it over K2CO3, filter, evaporate and dry the residue at 15mm, then recrystallise it from pet ether (b 40-60o), dry it at 25o/0.005mm and sublime it (sublimes slowly at room temperature)[Wittig & Pohmer Chem Ber 89 1334 1956, Gilman & Gorsich J Am Chem Soc 79 2625 1957]. [Beilstein 17 III/IV 548.]

InChI:InChI=1/C10H8O/c1-2-4-8-7(3-1)9-5-6-10(8)11-9/h1-6,9-10H

Upstream product

• 110-00-9 furan 
• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 925-90-6 ethylmagnesium bromide 
• 17051-75-1 o-chlorophenyl phenyl sulfoxide 
• 112921-53-6 ethyl (2-bromo)phenyl sulfoxide 
• 112921-52-5 o-bromophenyl phenyl sulfoxide 
• 67-56-1 methanol 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 75-05-8 acetonitrile 
• 1027537-24-1 (4-tetradecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 91-00-9 Benzhydrylamine 
• 75802-19-6 1-Ethoxy-1,3-dihydroisobenzofuran 

Downstream Products

• 612-94-2 2-phenylnaphthalene 
• 38648-94-1 1-phenyl-3a,4,9,9a-tetrahydro-1H-4,9-epoxido-naphtho[2,3-d][1,2,3]triazole 
• 30859-32-6 C₂₉H₂₄O₂ 
• 150988-77-5 1-(4-(naphthalen-2-yl)phenyl)ethan-1-one 
• 144951-18-8 C₂₀H₁₆N₂O₄ 
• 55240-76-1 1,8-Diphenyl-4,5:9,10-dibenzo-11,12-dioxa-4,9-tetracyclo<6.2.1.1^3.60^2,7>dodecadiene 
• 57969-57-0 1,8-Diphenyl-9,10-(2,2'-biphenylene)-4,5-benzo-12-oxa-4-tetracyclo<6.2.1.1^3,60^2,7>dodecen-11-one 
• 78048-54-1 C₃₁H₂₈O₂ 
• 144951-17-7 C₂₅H₁₈N₂O₄ 
• 3095-33-8 (naphthalen-1-yl)diphenylphosphine oxide 
• 28402-08-6 (naphthalen-2-yl)diphenylphosphine oxide 
• 85798-64-7 Isobenzofuran 

Relevant academic research and scientific papers

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

Improved solubility of hypervalent iodine-benzyne precursors: Synthesis and reaction of (phenyl)[2-(trimethylsilyl)phenyl]iodonium salts bearing long alkyl chains

Synthesis of new long-chained hypervalent iodine-benzyne precursors, (4-dodecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate and the tetradecyl derivative, is described. The benzyne precursors dissolve even in organic solvents of low polarity such as diethyl ether, THF, cyclopentyl methyl ether, benzene, and toluene. The trapping reactions with furan and tetraphenylcy-clopentadienone in the above solvent give the benzyne adducts in high yields without any loss of high reactivity of hypervalent iodine-benzyne precursors.

Synthesis, Solubility, and Reaction of Long Alkyl-Chained Hypervalent Iodine Benzyne Precursors

Long-chained hypervalent iodine benzyne precursors bearing ethyl, butyl, hexyl, octyl, decyl, dodecyl, and tetradecyl groups were synthesized, respectively. As the alkyl chain of the benzyne precursors is lengthened, the solubility in nonpolar organic solvents and the yield of the benzyne adduct with furan gradually increases.

Benzyne formation and the stepwise decomposition of benzenediazonium-2-carboxylate: A re-investigation

A study of the decomposition reactions of benzenediazonium-2-carboxylate, carried out in a number of mixed nucleophilic solvents, shows that a number of mechanistic pathways can operate simultaneously and can afford, in addition to products derived from benzyne, products derived from the 2-carboxyphenyl cation and the 2-carboxyphenyl radical: benzyne formation is favoured in halogenated solvents and occurs by the concerted loss of nitrogen and carbon dioxide.

A NEW SOURCE FOR GENERATION OF BENZYNE AND PYRIDYNE: REACTIONS OF O-HALOPHENYL (OR 3-BROMO-4-PYRIDYL) PHENYL SULFOXIDES WITH GRIGNARD REAGENTS

o-Chloro- and o-bromophenyl phenyl sulfoxides and (3-bromo-4-pyridyl) phenyl sulfoxide were treated with Grignard reagents to generate benzyne (or 3,4-pyridyne) in THF.The o-iodophenyl derivative, on the other hand, gave mainly o-(arylsulfinyl)phenyl Grignard reagent.

7-Oxabicyclohept-2-ene and Related Materials by Reductive Elimination

The cycloadduct 1 of furan and (E)-1,2-bis(phenylsulfonyl)ethylene has been converted to various derivatives which in turn have been subjected to sodium amalgam reductive elimination conditions.Some of these procedures constitute useful methods for the preparation of the title olefin.The amalgam reduction of 1 provides modest yields of 7-oxabicyclohepta-2,5-diene.The cycloadduct of isobenzofuran and the reactive dienophile was prepared and subjected to analogous reactions.Various reaction steps which compete with reductive elimination have been identified.