Influence of the branching of the dienophile on the Diels-Alder reaction with butadiene and its derivatives. I. Nitriles and methyl esters of acrylic and methacrylic acids was written by Doucet, Jeannine;Rumpf, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1954.Name: 4-Hydroxycyclohexanecarbonitrile This article mentions the following:
The Me group of methacrylic derivatives does not prevent the diene condensation but lowers yields and requires elevation of reaction T. The order of the following data are diene, dienophile, time in hrs., T鎺矯., product, b.p.鎺矯., n16D, % yield: (1) butadiene, Me acrylate, 5, 160, Me ester of 1-carboxy-3-cyclohexene, b15 72, 1.4635, 95; (2) butadiene, Me methacrylate, 8.5, 220, Me ester of 1-methyl-1-carboxycyclohex-3-ene, b16 73-5, 1.462, 65; (3) butadiene, acrylonitrile, 12,135, 1-cyano-3-cyclohexene, b20 83, 1.477, 83; (4) butadiene, methacrylonitrile, 13,180, 1-methyl-1-cyanocyclohex-3-ene, b20 83, 1.472, 53; (5) 2-ethoxybutadiene, Me acrylate, 5,160, Me ester of 1-carboxy-4-ethoxycyclohex-3-ene, b15 125-6, 1.464, 50; (6) 2-ethoxybutadiene, acrylonitrile, 12, 135-40, 1-cyano-4-ethoxycyclohex-3-ene, b15 125-6, n20D 1.4775, 90; (7) 2-ethoxybutadiene, methacrylonitrile, 12,180, 1-methyl-1-cyano-4-ethoxy-3-cyclohexene, b15 125-6, 1.478, 50; (8) chloroprene, Me acrylate, 5,160, Me ester of 1-carboxy-4-chlorocyclohex-3-ene, b15 109-11, 1.485, 60; (9) chloroprene, Me methacrylate, 9, 185-90, Me ester of 1-methyl-1-carboxy-4-chlorocyclo-3-hexene, b23 119-21, 1.491, 38; (10) chloroprene, acrylonitrile, 12,135, 1-cyano-4-chlorocyclohex-3-ene, b20 127-30, m. 54, no index of refraction, 34; (11) chloroprene, methacrylonitrile, 12,180, 1-methyl-1-cyano-4-chlorocyclohex-3-ene, b15 114-16, 1.511, 11. In connection with these studies the following compounds were reported: (a) acid chloride (b14 88鎺? and anhydride (b14 188-9鎺? of 1,2,5,6-tetrahydrobenzoic acid; (b) 1-methyl-1,2,5,6-tetrahydrobenzoic acid (m. 77鎺?, its acid chloride (b15 74-6鎺?, its amide (m. 87鎺?, its anhydride (b18 182鎺?; (c) 1-propionyl-1-methyl-3-cyclohexene (b20 96-7鎺? n 1.478), its 2,4-dinitrophenylhydrazone (m. 74.5鎺?, its hydrazone (b20 165鎺?, a condensation product of 2 mol of 1-propionyl-1-methyl-3-cyclohexene (b20 150鎺?; (d) 1-propionyl-1-methyl-3-cyclohexanol (b19 1 3-5鎺? and its p-nitrobenzoate (m. 194鎺?; (e) from 1,2,5,6-tetrahydrobenzonitrile and MeMgI (or EtMgBr) were formed ketones (b18 76鎺?and b16 84.5鎺? resp.), their semicarbazones m. 173.5鎺?and 147鎺?and their 2,4-dinitrophenylhydrazones m. 144鎺?and 141鎺? (f) 1-cyanocyclohexan-4-one (b12 139-41鎺? was made from 1-cyano-4-ethoxy-3-cyclohexene; (g) 1-cyanocyclohexan-4-ol (b12 153-4鎺? was made by reduction of 1-cyanocyclohexan-4-one. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Name: 4-Hydroxycyclohexanecarbonitrile).
4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Name: 4-Hydroxycyclohexanecarbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts