139313-45-4

Upstream product

• 1123-34-8 1-allyl-1-cyclohexanol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 108-94-1 cyclohexanone 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 5664-10-8 allylidenecyclohexane 
• 1713-63-9 cyclohexylideneacetaldehyde 
• 52376-48-4 1-cyclohexylidene-3-phenylpropane 

Relevant academic research and scientific papers

Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination

Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.

Organocatalytic Trapping of Elusive Carbon Dioxide Based Heterocycles by a Kinetically Controlled Cascade Process

A conceptually novel approach is described for the synthesis of six-membered cyclic carbonates derived from carbon dioxide. The approach utilizes homoallylic precursors that are converted into five-membered cyclic carbonates having a β-positioned alcohol group in one of the ring substituents. The activation of the pendent alcohol group through an N-heterocyclic base allows equilibration towards a thermodynamically disfavored six-membered carbonate analogue that can be trapped by an acylating agent. Various control experiments and computational analysis of this manifold are in line with a process that is primarily dictated by a kinetically controlled acylation step. This cascade process delivers an ample diversity of six-membered cyclic carbonates in excellent yields and chemoselectivities under mild reaction conditions.

Allylsamarium bromide-mediated cascade cyclization of homoallylic esters. Synthesis of 2-(2-hydroxyalkyl)cyclopropanols and 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols

In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive casc

Study on the coupling of acyclic esters with alkenes - The synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization-ring-opening- anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl) cyclopropanols from readily available materials.

Cobalt(II) Chloride Catalyzed Acylation of Alcohols with Acetic Anhydride: Scope and Mechanism

Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield.Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones.Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate.The β-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting β-acetoxy carbonyl compound is observed.A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene.A mechanism for these acylations is proposed by invoking an electron-transfer process.

A simple and inexpensive synthesis of 2-alkenals

A simple and inexpensive method for the C2 homologation of aldehydes and ketone to 2-alkenals consists of the reaction with allylmagnesium bromide, O-acylation of the resultant 1-alken-4-ol, and ozonolysis.