53963-38-5

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 42, p. 1808, 1994 DOI: 10.1248/cpb.42.1808

Upstream product

• 4364-06-1 cinnamaldehyde dimethylacetal 
• 762-72-1 allyl-trimethyl-silane 
• 1730-25-2 allylmagnesium bromide 

Relevant academic research and scientific papers

Aminium salt promoted catalytic substitution reactions of acetals with silylated nucleophiles

A catalytic amount of tris(p-bromophenyl)aminium hexachloroantimonate promoted the substitution reactions of dimethylacetals with various silylated nucleophiles through an electron transfer mechanism. Silyl compounds include silyl enol ether, ketene silyl

Pyrylium salt promoted substitution reactions of acetals with various silylated nucleophiles

Catalytic amounts of triarylpyrylium salts photochemically and thermally promoted the substitution reactions of dimethyl acetals with silylated nucleophiles.

Trimethylsilyl bis(fluorosulfonyl)imide: A New Catalyst for the Reactions of Acetals with Silyl Nucleophiles

A new catalyst trimethylsilyl bis(fluorosulfonyl)imide has been prepared for aldol type reactions and allylation of acetals.The catalyst has been found to be more active than trimethylsilyl triflate for the above reactions. - Key words: Trimethylsilyl bis

SOLID ACID-CATALYZED ALLYLATION OF ACETALS AND CARBONYL COMPOUNDS WITH ALLYLIC SILANES

Acetals and carbonyl compounds are allylated with allylic silanes in good yields in the presence of a catalytic amount of clay montmorillonite.

A FACILE SYNTHESIS OF HOMOALLYL ETHERS. THE REACTION OF ACETALS WITH ALLYLTRIMETHYLSILANES PROMOTED BY TRITYL PERCHLORATE OR DIPHENYLBORYL TRIFLATE

In the presence of a catalytic amount of trityl perchlorate or diphenylboryl triflate, acetals react smoothly with allyltrimethylsilanes to give the corresponding homoallyl ethers in good yields with good regio- and stereoselectivities.

Reaction of Acetals with Grignard Reagents

The reaction of dialkyl acetals derived from α,β-unsaturated aldehydes with Grignard reagents using TiCl4 in THF afforded the cross coupling products, allyl ethers, in high yields.The TiCl4-promoted reaction of alkyl 2,4-dichlorophenyl acetals, synthesized from 3,4-dihydro-2H-pyran or ethyl vinyl ether and 2,4-dichlorophenol, with Grignard reagents in THF at low temperature afforded the corresponding unsymmetrical ethers in high yields.When alkyl 2,4-dichlorophenyl acetals, synthesized from aromatic aldehyde or vinyl ethers and 2,4-dichlorophenol, were treated with Grignard reagents in benzene or toluene at room temperature in the absence of TiCl4, the cross coupling reaction took place and the corresponding ethers were isolated in good yields.

REGIOSPECIFIC ALLYLATION OF ACETALS WITH ALLYLSILANES CATALYZED BY IODOTRIMETHYLSILANE. SYNTHESIS OF HOMOALLYLETHERS

Allylation of acetals with allylsilanes is catalyzed by iodotrimethylsilane to give the corresponding homoallyl ethers, with regiospecific transposition of the allyl group.