156205-16-2Relevant academic research and scientific papers
Cage Enlargement of 1,4-Bis(hydroxymethyl)pentacyclo2,5.03,8.04,7>octane to a Tetracyclo3,9.04,7>nonane System in Formic Acid
Hasegawa, Takeshi,Kimura, Yoshihide,Kuwatani, Yoshiyuki,Higuchi, Hiroyuki,Hatanaka, Minoru,Ueda, Ikuo
, p. 462 - 472 (2007/10/02)
Cationic rearrangement of 1,4-bis(diarylhydroxymethyl)pentacyclooctanes (1) in formic acid gave new cage compounds, 8,8-diaryl-2-diarylmethylene-exo-5-(formyloxy)tetracyclononan-7-ols (3) and new cage-degradation products, 5,5-diaryl-4--2-cyclopenten-1-ones (4) along with Wagner-Meerwein rearrangement products, pentacyclodecanes (5; C 2 -bishomocubanes) and pentacyclodecanes (6; D 2h -bishomocubanes). 9,9-Diaryl-4-(diarylhydroxymethyl) pentacyclononan-1-ols (2) gave 4, 5, and 6 without the formation of 3.A Wagner-Meerwein 1,2-bond shift of 1 gave key intermediates 2 which were converted into 3 via homoallylic rearrangement, into 4 via pinacol-pinacolone-like rearrangement, or into 5 and 6 via Wagner-Meerwein rearrangement.
