32853-30-8Relevant articles and documents
Studies on ring-closing metathesis for the formation of the 11-membered ring system of daphnezomine C
Tanabe, Kazuhisa,Fujie, Ayako,Ohmori, Naoki,Hiraga, Yoshikazu,Kojima, Satoshi,Ohkata, Katsuo
, p. 1597 - 1604 (2007)
For the purpose of synthesizing daphnezomine C, model systems were examined to see if the ring-closing metathesis (RCM) reaction could be applied to prepare an 11-membered ring system bearing a tri-substituted alkene. As a result, it was found that the connectivity pattern of the tethers bearing the reacting alkene moieties was crucial. Thus, whereas a system involving a single 1,3- or 1,4-disubstituted cyclohexane derivative did not give RCM products, a flexible system without any rings between the two terminal alkenes gave the cyclic product with a yield of up to 65% using the second generation Grubbs catalyst.
Photochemistry of 1,5-hexadien-3-ones: Wavelength-dependent selectivity in intramolecular enone-olefin photoadditions
Dauben, William G.,Cogen, Jeffrey M.,Ganzer, George A.,Behar, Victor
, p. 5817 - 5824 (2007/10/02)
The photochemistry of ten 1,5-hexadien-3-ones in methanol is studied over the wavelength range of 313-366 nm, by using monochromatic light. With the goal of understanding the unusual wavelength-dependent selectivity observed for 5-methyl-1,5-hexadien-3-one (1), quantum yield measurements, structure reactivity studies, triplet sensitization, and quenching experiments are performed. While six of the ten dienones studied show selectivities that are independent of irradiation wavelength from 313 to 366 nm, four of the dienones exhibit wavelength-dependent selectivities that are similar to that observed in 1, thus establishing that 1 is not unique, as previously believed. Triplet sensitization studies suggest that the wavelength dependence results, largely, from a single-state α-cleavage reaction that competes with triplet cycloaddition. A variety of triplet quenchers were ineffective at inhibiting these reactions. Some possible mechanisms are discussed.
INTRAMOLECULAR PHOTOCYCLIZATION OF 1-(TRIMETHYLSILYL)-1,5-HEXADIEN-3-ONES
Wilson, Phyllis,Wolff, Steven,Agosta, William C.
, p. 5883 - 5886 (2007/10/02)
An influence upon the regiochemistry of cylization due to a 1-trimethylsilyl substituent is indicated upon comparison of the photochemistry of 4a,b and their carbon analogs 5a,b.