143015-71-8Relevant articles and documents
Facile synthesis of Z -alkenes via uphill catalysis
Singh, Kamaljeet,Staig, Shannon J.,Weaver, Jimmie D.
supporting information, p. 5275 - 5278 (2014/05/06)
Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.
Microwave-assisted minutes synthesis of bioactive phenylbutanoids occurring in Zingiber cassumunar
Joshi,Singh,Sharma,Sinha
, p. 370 - 373 (2007/10/03)
Microwave-assisted condensation of benzaldehyde (3a,b) with acetone in aqueous sodium hydroxide adsorbed on basic alumina provides phenylbutenone (4a-4b) in 68-71% yield within 4 min, which upon further reduction with sodium borohydride and basic alumina gives phenylbutenol (5a,b) in 91-94% yield within 2 min. Dehydration of 5 with anhydrous copper (II) sulfate gives phenylbutadiene (1a,b), a metabolite of Zingiber cassumunar, within 3 min in 42-48% yield, respectively. All the steps involve environmental friendly solvents and reagents, mild reaction conditions, and overall formation of product 1a,b from 3a,b in 34-38% yield within 9 min under microwave irradiation. 2005 Springer Science+Business Media, Inc.
