108186-34-1Relevant articles and documents
Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene: Stereochemistry of the Cycloadducts
Tsuda, Yoshisuke,Kiuchi, Fumiyuki,Umeda, Ikuno,Iwasa, Etsou,Sakai, Yuki
, p. 3614 - 3622 (2007/10/02)
Irradiation of a methanolic solution of 3-methoxycyclohexenone and ethoxyethylene with 254 nm light gave four stereoisomeric head-to-tail cycloadducts in the ratios indicated in Fig. 3.The structure and stereochemistry of all the isomers were determined by chemical correlations and spectroscopic means, respectively.The time-course product analysis suggested that, in this reaction, the exo and endo oriented ?-complexes are equally formed, both give the cycloadducts with a slight preference for antara-selectivity.The analogous cycloadduct of 3-aminocyclohexenone to ethoxyethylene decomposed into 2-ethoxycyclooctane-1,5-dione on silica gel chromatography.Keywords - photo-cycloaddition; stereochemistry; 3-methoxycyclohexanone; 3-aminocyclohexenone; acyclic olefin; 2+2 adduct; bicyclooctanone; cyclooctanedione; 2D NMR; time-course product analysis