The Condensation of Piperylene with Acrylonitrile and Methyl Acrylate

Abstract

When a diene such as piperylene (I) which possesses only one plane of symmetry undergoes the Diels-Alder reaction with an unsymmetrically substituted dienophile such as acrylonitrile (II) then possibly four different racemic nitriles might be formed. In this case these are cis-(III) and trans-1,2,5,6-tetrahydro-orf/to-tolunitrile (IV) and cis-(V) and trans-1,2,3,6-tetrahydro-meta-tolunitrile (VI). The possibility of the formation of

Stereochemistry of the Diels-Alder Reaction.

“…One difficulty previously mentioned is that the all-cis adducts are prone to isomerize to their more stable trans isomers under vigorous conditions. Some original reports of trans adducts from acyclic dienes have been corrected in recent years by showing that, at low temperatures and in the absence of equilibrating catalysts, the cis isomer predominates (54,55,207,208). Exceptions to the rule that cis adducts are formed are the írons-2-phenylcyclohexenecarboxylic acid derivatives resulting from the addition of ¿rons-1-phenyl-1,3-butadiene to acrylonitrile and acrylamide (207), and of methyl 1-phenyl-1,3-butadiene-2-carboxylate to acrylic acid (20).…”

Kinetics of Allyl-1,3,4-trimethylcyclo-hex-3-encarboxylate Obtaining

“…NMR spectrum was registered by the spectrometer Bruker AM-300 (300 MHz) in CDCl 3 using TMS as the internal standard 1. HNMR spectrum is in agreement with ATMC structure.…”

“…Lately alkylcyclohexene compounds have been used as a source for new base polymer materials. Multifunctional monomers with different structure and predetermined set of physical and chemical characteristics [1][2][3][4][5][6][7] were synthesized on their basis.…”

Synthesis of 1,3,4-trimethylcyclohex-3-en-1-carboxylic acid allyl ester

“…Effects of temperature, reaction duration, and ratio of reagents on the yield of 1,3,4-trimethylcyclohex-3-en-1-carboxylic acid allyl ester was studied. Optimal conditions of passing the process were found.Esters of alkyl-substutited cyclohexenecarboxylic acids are valuable raw material for the synthesis of a number of compounds including medical preparations, some of which inhibit cholesterin biosynthesis and noticeably reduce its level in blood [1]. Furthermore esters of alkylsubstutited cyclohexenecarboxylic acids are used for the synthesis of tertiary alcohols applied in perfumery compositions [2].…”

“…The mixture is stirred, put in an autoclave, and heated up for 6 h at 200°С in the presence of hydroquinone. The yield of the ester is 65% [1]. Methyl ester of 1,3,4-trimethylcyclohex-3-en-1-carboxylic acid is obtained by the cyclization of DMB with methyl metacrylate, using a solution of methyl metacrylate and DMB in toluene.…”