58568-20-0

Upstream product

• 5978-08-5 1-chloro-4-(1,3-dioxolane)-n-pentane 
• 108-94-1 cyclohexanone 

Downstream Products

• 58568-25-5 1-(Pentanon-4'-yl)-1-chlorcyclohexan 

Relevant academic research and scientific papers

Polymer supported naphthalene-catalysed lithiation reactions

The reaction of functionalised mono or dichlorinated materials 1a-6a with an excess of lithium and a catalytic amount of a naphthalene supported polymer (P-152, easily prepared by radical copolymerisation of 2-vinylnaphthalene, styrene and divinylbenzene) in THF either in the presence (Barbier-type conditions) or not of different electrophiles [Me3SiCl, Bu(n)CHO, Bu(i)CHO, PhCHO, Et2CO, c(C3H5)2CO, Pr(i)2CO, (CH2)4CO, (CH2)5CO, PhCOMe, PhCH=NPh] leads, after hydrolysis, to the expected products 1c-6c. The catalyst is quantitatively recovered and can be reused several times without any loss of its activity.

Polymer supported naphthalene-catalysed sodium reactions

Arene-catalysed sodium reactions have been utilised in the generation of organosodium complexes, from a variety of organochloride complexes, in high yield. Phenyltrimethylsilane, benzene and 2-methyl-1-phenyl-1-propanol were prepared in yields >80%, using polymer supported naphthalene-catalysed sodium reactions, whereby phenylsodium, prepared from the reaction of chlorobenzene, sodium powder and polymer-supported naphthalene (5-100%), was quenched with chlorotrimethylsilane, water or PriCHO respectively. The Royal Society of Chemistry.

Polyphenylene as an electron transfer catalyst in lithiation processes

The lithiation of different functionalised chlorinated materials (1a-c), dichlorinated compounds (1d-f) and benzofused cyclic ethers (1g,h) with lithium powder in the presence of catalytic amounts of either linear (LPP) or crosslinked (CPP) polyphenylene, in THF at temperatures ranging between -78 and 20°C, leads to the expected organolithium intermediates (Ia-h), which by reaction with electrophiles [ButCHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe, Me3SiCl] gives, after hydrolysis with water, the expected products 2aa-hf.

Polymer supported arene-catalysed lithiation reactions

The reaction of functionalised mono or dichlorinated materials 1a-6a with an excess of lithium and a catalytic amount of a naphthalene (P(N)) or biphenyl (P(B)) supported polymer (easily prepared by radical copolymerisation of 2-vinylnaphthalene or 4-vinylbiphenyl with vinylbenzene and divinylbenzene) in THF either in the presence or not of different electrophiles [Me3SiCl, (i)prCHO, PhCHO, Et2CO, (CH2)4CO, (CH2)5CO, (c- C3H5)2CO, (i)Pr2CO, PhCOMe, PhCH=NPh] at -78 or -50°C leads, after hydrolysis with water, to the expected functionalised products 1ca-6ck. The polymeric catalyst is quantitatively recovered and can reused several times without any loss of activity.

Arene-catalysed Lithiation Reactions with Lithium at Low Temperature

The reaction of functionalized alkyl chlorides or phenyl sulphides with an excess of lithium powder in the presence of a catalytic amount of an arene (1percent; naphthalene, biphenyl, 4,4'-di-tert-butylbiphenyl) in tetrahydrofuran (THF) at -78 deg C gives the corresponding organolithium compounds, which react with electrophiles such as water, iso-butyraldehyde, or cyclohexanone to yield the expected reaction products.

Masked Lithium Bishomoenolates: Useful Intermediates in Organic Synthesis

The lithiation of the chloro ketals 9 with lithium naphthalenide at -78 deg C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCOH, Ph

2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds

2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at -78°C. The reaction of these masked bishomoenolates with different electrophiles yie