Bicyclic azoalkanes via urazoles derived from cycloaddition of N-phenyl-1,2,4-triazoline-3,5-dione with strained bicycloalkenes

The efficient synthesis of N-fused coronene analogs and a related polyimide with near-infrared absorption

“…The addition of chloranyl led to the oxidative re-aromatization of the adducts and shifted the reversible cycloaddition. The bis-adduct has an interesting structure and produces an N-heterocyclic analog of coronene, which would be generated through a ring-opening reaction, 19 in Table 1. The reaction was performed under refluxing xylene for the favorable thermal aromatization of a nonaromatic intermediate.…”

(1RS,8SR,9RS,10RS,11RS,12RS)-10,11-Dibromotetracyclo[6.4.2.02,7.09,12]tetradeca-2,4,6,13-tetraene

“…Benzobarrelene systems afford the possibility of several mechanistically interesting investigations. These compounds are intriguing in view of the di-%-methane rearrangement (Zimmerman, 1980;Zimmerman et al, 1968), solvolytic reactivity (Barkhash, 1984;Menzek, 2000) and versatile applications (Hales et al, 1995;Erden & de Meijere, 1983;Adam et al, 1980;Paquette & Volz, 1976). In view of these factors, substituted benzobarrelene derivatives are important compounds that can provide information about how substituents will in¯uence the reaction modes (Altundas Ë & Balcõ, 1997).…”

Reaction of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD) with bicyclic monoterpenes

“…A particularly illustrative example is a-pinene (5) and P-pinene (6). Thus, while a-pinene gives some dipolar addition and mainly ene-reaction, for P-pinene only ene-reaction takes place.…”