An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies

• Main Authors: Mohamed Husaini Abdul Rahman, Ramabhadran, Raghunath O., Collier, Steven J., Storr, Richard C., Bates, Roderick Wayland
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2019
• Subjects: Claisen Rearrangement; Cycloaddition; DRNTU::Science::Chemistry
• Online Access: https://hdl.handle.net/10356/90300; http://hdl.handle.net/10220/48476
• Institution: Nanyang Technological University

Trapping of a pyrimidinone-derived o-quinodimethane with tetraphenylcyclopentadienone gives a mixture of the [4 + 2] and formal [4 + 4] adducts. Computational studies show that the latter arises by a sequence of [4 + 2] cycloaddition, homolysis, radical recombination to a spiro-tetrahydrofuran and C...