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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Published on: November 9, 2019

CAAC-Based Thiele and Schlenk Hydrocarbons.

Avijit Maiti¹, Jessica Stubbe², Nicolás I Neuman^2,3

¹Tata Institute of Fundamental Research (TIFR) Hyderabad, Gopanpally, Hyderabad-500107, Telangana, India.

Angewandte Chemie (International Ed. in English)

|January 22, 2020

Summary

Researchers synthesized novel diradicals, analogues of Thiele's and Schlenk's hydrocarbons, using cyclic(alkyl)(amino)carbenes. One diradical exhibits a singlet ground state, while the other forms a dimer, showcasing a new method for redox-active compounds.

Keywords:

Carbenes conjugation dimerization radicals structure elucidation

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Published on: September 18, 2016

Area of Science:

Organic Chemistry
Diradical Chemistry

Background:

Diradicals have been studied for over a century, with early examples including Thiele's and Schlenk's hydrocarbons.
Cyclic(alkyl)(amino)carbenes (CAACs) are versatile organic compounds with unique electronic properties.

Purpose of the Study:

To synthesize novel CAAC analogues of Thiele's and Schlenk's hydrocarbons without using CAAC precursors.
To investigate the electronic properties and reactivity of these new diradical compounds.

Main Methods:

Direct synthesis of diradicals, avoiding CAAC precursors.
Characterization of the synthesized diradicals to determine their ground states and reactivity.

Main Results:

The CAAC analogue of Thiele's hydrocarbon was found to have a singlet ground state.
The CAAC analogue of Schlenk's hydrocarbon exists as a diradical with two unpaired electrons.
The Schlenk's hydrocarbon analogue undergoes intermolecular double head-to-tail dimerization.

Conclusions:

A straightforward and modular synthetic methodology for generating novel diradicals has been established.
This method provides access to both Kekulé and non-Kekulé diradicals.
The developed approach can be extended for the synthesis of other redox-active organic compounds.