81423-64-5Relevant academic research and scientific papers
REACTIVITY OF PENT-1-EN-4-YNES AND SYNTHESIS OF 2-SUBSTITUTED DERIVATIVES
Drewes, Siegfried E.,Slater-Kinghorn, Barbara J.
, p. 603 - 610 (2007/10/02)
The synthesis of some 2-substituted pent-1-en-4-ynes via an SN1 reaction is described.Using dicobalt octacarbonyl as protecting group, selective bromination of 1,5-diphenylpent-1en-4-yne is achieved.
Reactions of Vinylphosphonates. 2. Synthesis of Functionalized Dienes, Trienes, and Their Analogues. Synthetic Aplications to Regioselectively Functionalized Benzene Derivatives
Minami, Toru,Nishimura, Katsuhide,Hirao, Ichiro,Suganuma, Hiroyuki,Agawa, Toshio
, p. 2360 - 2363 (2007/10/02)
The phosphoryl-stabilized carboanions prepared from vinylphosphonates 1a,b and various carbanions 2a-c react with aldehydes 3 to give olefins having various functional groups.The dienes 5c-g produced by the reaction using α,β-unsaturated aldehydes and a methyl (methylsulfinyl)methyl sulfide carbanion (2b) easily undergo thermolysis to afford reactive intermediate 1-methylthio 1,3,5-trienes, which are converted into the 1,4-disubstituted benzenes 7a-e in 27-56percent overall isolated yields via the electrocyclic reaction into cyclohexadienes and subsequent elimination of methanethiol.Thermolysis of the reaction product using ethyl α-(diethylphosphono)acrylate (1a), 2b, and 1,4-bis(2-formylethenyl)benzene (3g) produces 4,4''-bis(ethoxycarbonyl)-1,1':4',1''-terphenyl (7f) in 16percent yield.The reaction using an ethyl (methylthio)acetate carbanion (2c) instead of 2b gives thermally stable dienes 5i-l in 38-52percent yields.Oxidation of the dienes 5i,k,l followed by thermolysis, leads to the 1,2,4-trisubstituted (8a,b) and 1,2-disubstituted benzenes (9).Similar treatment of the product 5m derived from 1a, 2c, and 3-phenylpropargylaldehyde (3f) produces a mixture of 2,4-bis(ethoxycarbonyl)biphenyl (8a) and ethyl 4-(ethoxycarbonyl)-7-phenylhepta-2,4-dien-6-ynoate (11) in 23percent and 32percent yields.
