SOS Case Study: Discovering an Improved Synthetic Route to [1.1.1]Propellane

Kasmita Singha | IISc Bangalore, India

Kasmita Singha is currently pursuing a BS-MS degree at the Indian Institute of Science Education and Research (IISER) in Bhopal, India. After completing internships at IISER Bhopal and IIT Guwahati, she joined Dr. Durga Prasad Hari’s research group at the Indian Institute of Science (IISc) in Bangalore to work on her BS project, focusing on the topic of ring-strain chemistry.

Abstract:

We are interested in exploring new reactivity modes of [1.1.1]propellane. The most extensively studied aspect of the reactivity of propellanes involves the functionalization of the bridgehead carbon atoms, which allows for 1,3-difunctionalization, leading to the formation of bicyclo[1.1.1]pentanes. Our group has recently utilized the carbene reactivity of [1.1.1]propellane for [2,3]-sigmatropic rearrangements.

A search in Science of Synthesis quickly revealed several key references detailing the preparation of [1.1.1]propellane. The conditions reported in these references allowed us to achieve a better yield than in our previous attempts.