RT Conference Proceedings
T1 Contractive annulation – A new strategy for the synthesis of small strained cyclophanes
A1 Bodwell, Graham J.
K1 Ciclofanos
K1 Reactividad (Química)
AB Contractive annulation was recently developed in our group as a new strategy for the synthesis of small,strained cyclophanes. The crux of the strategy is that a bridge atom is used in the π-extension of anaromatic ring in an existing cyclophane. As such, the growth of the aromatic system is necessarilyaccompanied by the contraction of the bridge. This brings with it an increase in molecular strain. A keyfeature of contractive annulation is that aromatic stabilization energy is used to counterbalance theincrease in strain energy.Contractive annulation was first used successfully in the synthesis of [2.1]naphthalenophane 2 from[2.2]paracyclophane (1).1 It was subsequently demonstrated that it could be applied in a two-directionalfashion in the synthesis of [1.1]naphthalenophane 3.2 Opportunities abound for the further developmentof the contractive annulation strategy, using not only [2.2]paracyclophane (1) as a starting material, butalso other cyclophanes such as the [n](2,7)pyrenophanes, e.g. [8](2,7)pyrenophane (4). Singlecontractive annulation of 4 would lead to benzopyrenophane 5 and double contractive annulation wouldafford dibenzopyrenophanes 6 and 7. Progress toward the achievement of these objectives will bepresented.
YR 2023
FD 2023
LK https://hdl.handle.net/10630/28098
UL https://hdl.handle.net/10630/28098
LA eng
NO Conferencia científica
NO Departamento de Química FísicaPrograma de doctorado en Química y Tecnología químicaUniversidad de Málaga. Campus de Excelencia Internacional Andalucía Tech.
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 6 mar 2026