3618-18-6

Upstream product

• 502-49-8 cycloactanone 
• 83587-38-6 N,N,P-trimethyl-P-phenylphosphinothioic amide 
• 55373-76-7 1-ethynylcyclooctan-1-ol 
• 65-85-0 benzoic acid 
• 931-88-4 cis-Cyclooctene 
• 931-88-4 1,2-cyclooctene 

Downstream Products

• 933-11-9 methylcyclooctene 
• 1185742-73-7 C₂₇H₃₅NO₂ 
• 3637-63-6 cyclooctylmethanol 
• 1616882-72-4 C₁₆H₂₁NO₃ 
• 59123-41-0 1-methylcyclooctanol 
• 15840-64-9 1-methylcyclooctene 

Relevant academic research and scientific papers

Mechanism-based design and optimization of a catalytic electrophilic cyclopropanation without diazomethane

Iodomethylboron compounds, either the trifluoroborate or a boronic ester, cyclopropanate electron-rich olefins and unprotected allylic alcohols with Pd catalysts according to a novel, designed catalytic cycle. Proposed intermediates in a "diverted Heck" mechanism are observed by means of spectroscopic studies and by isolation and X-ray crystallographic characterization, which together with reaction kinetics point to a separation of rate-determining and product-determining steps, and a mechanism-based optimization of the yield, selectivity, and scope of the catalytic electrophilic cyclopropanation. The reaction with crystalline, air-stable, nonhygroscopic, and nontoxic reagents provides an alternative to Simmons-Smith-type reactions, as well as cyclopropanation procedures that require the use of diazomethane.

CYCLOPROPANATION

A method of preparing a cyclopropane ring-bearing compound of the formula (I) in which R1 and R2 are independently selected from C1-C10 alky], optionally substituted, or R1 and R2 together with the bonds linking them to the cyclopropane ring, form a monocyclic or bicyciic ring system, which may comprise at least one hetero-atom, comprising the reaction of a compound of formula (II) in which R1 and R2 have the significances hereinabove defined, with a compound of formula (III) in which X is selected a nucieofuge selected from halides and pseudohalides and Y is an electro flige selected from boranes and borates, in the presence of a metal catalyst complex selected from those that a useful for catalytic cyclopropanation and those useful for catalyzing Heck coupling. The method prov ides a particularly easy and non-hazardous method of cyclopropanation.

A palladium-catalyzed methylenation of olefins using halomethylboronate reagents

Methylenation of electron-rich olefins is a highly challenging reaction, for which we have developed a new methodology exploiting Pd-catalysis and halomethylboronate reagents, the latter replacing diazomethane and zinc carbenoids as methylene donors. Optimization of the reaction for norbornene and extension to several other olefins are reported, with reasonable-to-excellent yields of cyclopropanes in combination with β-H elimination products. Several mechanisms are plausible for this methylenation reaction.

Ruthenium(IV)-catalyzed markovnikov addition of carboxylic acids to terminal alkynes in aqueous medium

The dimeric bis(allyl)ruthenium(IV) complex [{RuCl(μ-Cl)( η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) (5) and several mononuclear species trans-[RuCl2(η3: η3-C10H16)(L)] (L = two-electron-donor ligand) (6) derived from 5 have been checked as catalysts for the addition of carboxylic acids onto terminal alkynes using water as a green reaction medium. The best results in terms of activity and regioselectivity were obtained with the mononuclear derivative trans-[RuCl2(η3: η3-C10H16)(PPh3)] (6a), which was able to promote the selective Markovnikov addition of both aromatic and aliphatic carboxylic acids to a large variety of terminal alkynes, enynes, and diynes as well as propargylic alcohols. In this way, a wide number of enol esters and β-oxo esters could be synthesized in moderate to good yields under mild conditions (60 °C) in an aqueous medium.