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Functionalization of Carborane via Carboryne Intermediates pp 73–85Cite as

Reaction of o-Carboryne with Nitrones: A Formal [5 + 2] Cycloaddition

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Abstract

This chapter details the first example of transition-metal-free [5 + 2] cycloaddition of nitrones with o-carboryne. In this process, the nitrone moieties served as five-atom building blocks with both heteroatoms being incorporated into the framework of the final products. Mechanistic studies suggest that the N–O bond cleavage in the initially formed [3 + 2] cycloadducts, followed by an intramolecular nucleophilic addition, and rearomatization leads to the final products. This approach allows rapid construction of o-carborane-fused seven-membered heterocycles with a broad substrate scope, which also provides new insight into the chemistry of nitrones.

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  1. Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Hong Kong, Hong Kong

    Da Zhao

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Zhao, D. (2016). Reaction of o-Carboryne with Nitrones: A Formal [5 + 2] Cycloaddition. In: Functionalization of Carborane via Carboryne Intermediates. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-10-1569-4_4

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