Related Experiment Video
Updated: Nov 21, 2025
![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
Cleavage of C-O and C-H bonds in ethers by a genuine Si[double bond, length as m-dash]O bond
Ryo Kobayashi1, Shintaro Ishida1, Takeaki Iwamoto1
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. takeaki.iwamoto@tohoku.ac.jp.
Abstract:
An isolable three-coordinate dialkylsilanone without substantial electronic stabilization reacts with several ethers resulting in the cleavage of the C-O or C-H and C-O bonds in the ethers which have not been observed for the hitherto-known electronically stabilised isolable Si[double bond, length as m-dash]O species. The formation of the Lewis base (DMAP and MTHP) complexes of the dialkylsilanone and the DFT calculations elucidated that the coordination of the ethereal oxygen atom to the Lewis acidic Si atom of the genuine Si[double bond, length as m-dash]O bond is a key interaction for the reaction.
More Related Videos
Related Concept Videos
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...
Ethers to Alkyl Halides: Acidic Cleavage
Physical Properties of Ethers
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
Structure and Nomenclature of Epoxides
Hybridization of Atomic Orbitals II
Crown Ethers

