Related Experiment Video
Updated: May 21, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
(2R,4R)-4-(2-Eth-oxy-2-oxoeth-yl)-2,6,6-trimeth-yl-2-oxo-1,3,6,2λ(5)-dioxaza-phospho-can-6-ium iodide
Bradford W Fulfer1, Frank R Fronczek, Steven F Watkins
1Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA.
Abstract:
The title compound, C(11)H(23)NO(5)P(+)·I(-), consists of an eight-membered cationic heterocyclic ring in a boat-chair conformation. The ring features a tetra-alkyl-ammonium N and a methyl-phospho-nate P atom. A -CH(2)(CO)OC(2)H(5) ester side chain at the C adjacent to oxygen produces two chiral centers at that substituted C atom and the P atom, both of which were determined to have absolute R,R configurations. A previously determined racemic bromide analog has exactly the same ring but with a -C(15)H(31) side chain. In that structure, both chiral centers show the same relative R/S,R/S configurations, but the ring in the bromide analog is in a boat conformation.
Related Concept Videos
Structure and Nomenclature of Epoxides
Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Crown Ethers
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Predicting Molecular Geometry
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
