163798-41-2

Upstream product

• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 663155-32-6 ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate 
• 110481-61-3 3-trimethylsilyl-2-diethylphosphonopropionic acid ethyl ester 

Downstream Products

• 1039704-25-0 2-(cyclohex-1-en-1yl)methylprop-2-enoic acid 
• 1039704-23-8 (2Z)-3-(cyclohex-1-en-1-yl)-2-methylprop-2-enoic acid 
• 663155-47-3 (E)-3-(cyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-en-1-ol 

Relevant academic research and scientific papers

Correlation of hydrolysis and desilylation of 2-[(trimethylsilyl)methyl] acrylate derivatives in aqueous alkali solutions

Hydrolysis and desilylation reaction of 2-[(trimethylsilyl)methyl]acrylate (=2-[(trimethylsilyl)methyl] prop-2-enoate) derivatives were studied to evaluate the effect of the presence/absence of a further conjugating substituent (Schemes 3 and 4 and Tables 1 and 2). The substrates having a nonconjugating substituent at the acrylate moiety were stable to dilute alkali conditions, and afforded simple hydrolysis products under concentrated alkali conditions. In contrast, both hydrolysis and desilylation occurred from the substrates bearing conjugated substituents at the acrylate skeleton. The difference in reactivity can be explained in terms of the stabilization of the intermediate anion.

An Acylative C-C Single-Bond Cleavage and a Self-Cyclization of Ethyl 2-(Trimethylsilylmethyl)penta-2,4-dienoate or Its Free Acid under Ritter Condition

An acylative C(3)-C(4)-bond cleavage of ethyl 4,5-disubstituted 2-(trimethylsilylmethyl)penta-2,4-dienoate occurred to give an ethyl 2-(2-oxoalkyl)acrylate by treatment with trifluoromethanesulfonic acid in nitriles. A self-cyclization also occurred to give a 5,5-disubstituted 3-methylenetetrahydrofuran-2-one when the reactions were carried out in bulky nitriles. Only self-cyclization proceeded when the corresponding 4,5-disubstituted 2-(trimethylsilylmethyl)penta-2,4-dienoic acid was treated in acetonitrile. The reaction mechanism is described.