17448-96-3Relevant articles and documents
High Pressure Mediated Diels-Alder Reaction of Furan with Dialkyl (Acetoxymethylene)malonate
Sera, Akira,Ohara, Meguru,Kubo, Toshiaki,Itoh, Kuniaki,Yamada, Hiroaki,et al.
, p. 5460 - 5464 (1988)
The Diels-Alder reaction of furan with dialkyl (acetoxymethylene)malonates 1 did not proceed even in the presence of Lewis acid catalysts under conventional conditions.However, the reaction under high pressure (1.1 GPa) gave the expected cycloadducts, dialkyl 3-acetoxy-7-oxabicyclohept-5-ene-2,2-dicarboxylates 2.The bis-, tris-, and tetrakisadducts 3-6 were also produced in some amounts.Similar high-pressure reactions in the presence of zinc iodide as a catalyst yielded dialkyl 2-furfurylidenemalonate 8, and none of the adducts were obtained.
α,β-Unsaturated esters from the tri-n-butylarsine-promoted reaction of bromomalonic esters with aldehydes
Shen, Yanchang,Yang, Baozhen
, p. 45 - 50 (1989)
A convenient synthesis of α,β-unsaturated esters (in 68-96percent yields) from the reaction of a bromomalonic ester with aldehydes promoted by tri-n-butylarsine is descriebed.A mechanism involving halophilic attack of tri-n-butylarsine leading to the formation of a salt followed by reaction with carbonyl compounds is proposed.This methodology provides a convenient route to α,β-unsaturated esters and represents an alternative to the Knoevenagel reaction.
Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations
Delbrassinne, Arnaud,Richald, Maximilien,Janssens, Julien,Robiette, Rapha?l
supporting information, p. 2862 - 2868 (2021/06/11)
Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituents. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.
Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 10153 - 10157 (2019/12/26)
An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.