Naslov
Syn-facial hetero-bridged [n]polynorbornanes: a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes

Autori
Warrener, Ronald, N. ; Margetić, Davor ; Foley Patrick, J. ; Butler, Douglas, N. ; Winling, Alain ; Beales, Kerry, A. ; Russell, Richard, A.

Izvornik
Tetrahedron (0040-4020) 57 (2001), 3; 571-582

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
cycloadditions; epoxides; mechanisms; polycyclic aliphatic compounds; 1;3;4-oxadiazoles

Sažetak
New oxygen-bridged norbornane-fused cyclobutene epoxides and bis-(cyclobutene epoxides) are described and shown to react stereoselectively with 7-azanorbornenes to produce syn-facial N,O-bridged polynorbornanes and stereorandomly with 7-oxanorbornenes to produce O,O-bridged polynorbornanes as mixtures of syn-facial and anti-facial products.(1) Polarofacial systems containing up to six syn-facial norbornane bridges are described, while systems with seven co-facial oxygen atoms have been prepared by incorporating terminal epoxide rings to O-5-[5]polynorbornanes. Ester-substituted 1,3,4-oxadiazoles are shown to be useful reagents for coupling 7-oxanorbornanes and produce predominantly syn-facial O-bridged polarofacial systems together with their anti-facial isomers.

Izvorni jezik
Engleski

POVEZANOST RADA