134916-71-5

Basic information

• Product Name: (1,2-diacetoxyethyl)cyclohexane
• Synonyms: (1,2-diacetoxyethyl)cyclohexane
• CAS NO: 134916-71-5
• Molecular Weight: 228.288
• Mol File: 134916-71-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1,2-diacetoxyethyl)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1,2-diacetoxyethyl)cyclohexane(134916-71-5)
• EPA Substance Registry System: (1,2-diacetoxyethyl)cyclohexane(134916-71-5)

Safety Data

• Hazardous Substances Data: 134916-71-5(Hazardous Substances Data)

Upstream product

• 695-12-5 vinylcyclohexane 
• 108-24-7 acetic anhydride 
• 56697-99-5 2-cyclohexyl-2-acetoxyacetaldehyde 
• 590-97-6 acetoxymethyl bromide 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 61414-09-3 1-cyclohexylethane-1,2-diol 

Relevant articles and documents

Mechanistically Driven Development of an Iron Catalyst for Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen Peroxide

Product release is the rate-determining step in the arene syn-dihydroxylation reaction taking place at Rieske oxygenase enzymes and is regarded as a difficult problem to be resolved in the design of iron catalysts for olefin syn-dihydroxylation with potential utility in organic synthesis. Toward this end, in this work a novel catalyst bearing a sterically encumbered tetradentate ligand based in the tpa (tpa = tris(2-methylpyridyl)amine) scaffold, [FeII(CF3SO3)2(5-tips3tpa)], 1 has been designed. The steric demand of the ligand was envisioned as a key element to support a high catalytic activity by isolating the metal center, preventing bimolecular decomposition paths and facilitating product release. In synergistic combination with a Lewis acid that helps sequestering the product, 1 provides good to excellent yields of diol products (up to 97% isolated yield), in short reaction times under mild experimental conditions using a slight excess (1.5 equiv) of aqueous hydrogen peroxide, from the oxidation of a broad range of olefins. Predictable site selective syn-dihydroxylation of diolefins is shown. The encumbered nature of the ligand also provides a unique tool that has been used in combination with isotopic analysis to define the nature of the active species and the mechanism of activation of H2O2. Furthermore, 1 is shown to be a competent synthetic tool for preparing O-labeled diols using water as oxygen source.

A DIRECT PREPARATION OF 1,2-DIACETATES FROM ALDEHYDES AND KETONES PROMOTED BY SAMARIUM DIIODIDE

In a mild reaction mediated by samarium diiodide, ketones and aldehydes have been converted into 1,2-diacetates from commercially available bromomethyl acetate in a single synthetic transformation.