16133-73-6

Upstream product

• 108-94-1 cyclohexanone 
• 34164-50-6 4-penten-1-ylmagnesium bromide 
• 1119-51-3 bromopentene 
• 17247-58-4 (Bromomethyl)cyclobutane 

Downstream Products

• 16133-74-7 1-pent-4-enylcyclohexyl acetate 
• 727665-33-0 4-(1-hydroxy-1-cyclohexyl)-2-methylenebutyric acid 
• 727665-27-2 1-(3-formylbut-3-enyl)cyclohexyl acetate 
• 180-43-8 spiro[5.5]undecane 
• 70079-77-5 2-(4-pentenyl)-2-cyclohexen-1-one 
• 70079-75-3 3-(4-pentenyl)-2-cyclohexen-1-one 
• 4481-78-1 1-oxa-spiro[5.5]undecan-2-one 
• 113345-13-4 2-<<(p-methoxyphenyl)telluro>methyl>-1-oxaspiro<5.5>undecane 
• 113345-12-3 1-<2-acetoxy-3-<(p-methoxyphenyl)telluro>propyl>cyclohexyl acetate 
• 16133-75-8 1-(Penten-⁽⁴⁾-yl)-cyclohexen 

Relevant academic research and scientific papers

Cyclopropylmethyl- and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity

The reaction of (chloromethyl)cyclopropane 5 and (bromomethyl)cyclobutane 8 with lithium and a substoichiometric amount of DTBB, in the presence of different carbonyl compounds as electrophiles, in THF at -78 °C leads, after hydrolysis, to the corresponding cycloalkyl alcohols 6 and 9, respectively. However, when the same starting materials are lithiated using naphthalene as catalyst in diethyl ether and at higher temperature (0 or 25 °C), and then react with the same electrophiles, the final hydrolysis yields the corresponding unsaturated alcohols 7 and 10, respectively.

Dibromomethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4, which could be further converted to the corresponding α-keto esters A-5. This methodology can be also applied to the preparation of α-methylene lactones B-4, α-methylene lactams, and α-keto lactones B-5 with various ring sizes.

Synthesis of spiranic heterocycles by induced decomposition of unsaturated peroxides

Induced decomposition of unsaturated peroxides in a good hydrogen-donor solvent leads to the functionalization of the latter.If the peroxide contains a cycle on the carbon next to the O-O bond, the reaction gives spirans with an oxiran, an oxetan or a tetrahydrofuran ring in good or even excellent yields.Keywords: unsaturated peroxide / spiranic heterocycles / induced decomposition / homolytic intramolecular substitution / radical addition

Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes.

Treatment of tertiary γ- and δ-hydroxyalkenes with chromium trioxide in acetic acid/acetic anhydride gives reasonable yields of γ- and δ-lactones by oxidative cyclization, with loss of one carbon. A mechanism is proposed involving formation of a chromate monoester, followed by intramolecular oxidative attack on the alkene.