87371-57-1Relevant academic research and scientific papers
Diels-Alder Reaction of 6,6-Dimethylfulvene with 2-Acetoxyacrylonitrile. Preparation of 5-(2-Hydroxyethyl)-2-cyclopenten-1-one
Oku, Akira,Nozaki, Yohko,Hasegawa, Hiroshi,Nishimura, Jun,Harada, Toshiro
, p. 4374 - 4377 (2007/10/02)
The Diels-Alder reaction of 6,6-dimethylfulvene with 2-acetoxyacrylonitrile gave two different adducts, 2-acetoxy-2-cyano-7,7-isopropylidenebicyclohept-5-ene (3, 70percent) and 2-acetoxy-2-cyano-1-isopropenylbicyclohept-5-ene (4, 18percent).The formation of 4, which has not been reported before, can be suppressed by adding pyridine to the reaction mixture.Hydrolysis of 3 by sodium methoxide, followed by successive treatment with unsolvated hydroxide ion, peroxyformic acid, lithium aluminum hydride, and lead tetraacetate, gave 5-(2-hydroxyethyl)-2-cyclopenten-1-one (15, 35percent from 3).
