81149-95-3

Upstream product

• 14036-06-7 diethoxymethyl acetate 
• 108-86-1 bromobenzene 
• 127921-65-7 (Z)-1-tributylstannyl-3,3-diethoxyprop-1-ene 
• 5344-23-0 diethoxyacetaldehyde 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 71276-94-3 (2,2-Diethoxyethyliden)triphenylphosphoran 
• 100-52-7 benzaldehyde 
• 74-96-4 ethyl bromide 
• 64-17-5 ethanol 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 

Downstream Products

• 14371-10-9 (E)-3-phenylpropenal 
• 57194-69-1 cinnamaldehyde 
• 1041854-48-1 tert-butyl (R)-1-((1S,2E)-1-ethoxy-3-phenylallyl)-2-oxocyclohexanecarboxylate 

Relevant academic research and scientific papers

An Efficient Access to (Z)-Vinyltin Acetals via Titanation of the Corresponding Alkynyltins

Titanation of alkynyltin acetals has been exploited to obtain the corresponding (Z)-disubstituted vinyltins and γ-hydroxy trisubstituted vinyltins, as a single geometrical isomer.

Substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents: a route to allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals

The substitution of the acetoxy groups of dialkoxymethylacetates by organometallic reagents has been examined in a search for new methods of preparing functional acetals.The efficiency of the substitution of the acetoxy group is highly dependent on the nature of the organometallic reagents: soft nucleophiles with strong electrophilic assistance by the counterion are the best reagents.Allyl-, propargyl-, homoallyl-, homopropargyl- and α-stannylacetals have been made by this route, in which dialkoxymethylacetates often function as useful substitutes for dialkylphenylorthoformates.

Reactions with Phosphine Alkylenes, 44. A Further Synthesis of (Z)-α,β-Unsaturated Aldehydes

Reaction of phosphorus ylides 4, especially such with electron donating groups R, with the glyoxal semiacetal 5 leads Z-stereospecifically to the formation of the acetals 3, which can be cleaved to the (Z)-α,β-unsaturated aldehydes 6.

Cumulated Ylides, XII. A Stereoselective Synthetic Method for (Z)-α,β-Unsaturated Aldehydes

(2-Ethoxyvinyl)triphenylphosphonium bromide (5) is converted with sodium amide into the corresponding phosphaallenylide 6 which adds ethanol forming the ylide 7. 7 is also obtained by the reaction of 5 with sodium ethanolate.The Wittig reaction of 7 with aldehydes 2 proceeds with high (Z)-stereoselectivity to give (Z)-α,β-unsaturated acetals 8 which are cleaved under well defined conditions with p-toluenesulfonic acid or with wet silica gel to (Z)-α,β-unsaturated aldehydes 9.