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J Am Chem Soc. 2011 Aug 24;133(33):13006-9. doi: 10.1021/ja206497x. Epub 2011 Aug 2.

1,2-BN cyclohexane: synthesis, structure, dynamics, and reactivity.

Author information

1
Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.

Abstract

BN/CC isosterism has emerged as a viable strategy to increase the structural diversity of carbon-based compounds. We present the first synthesis and characterization of the parent 1,2-BN cyclohexane, the BN-isostere of cyclohexane. 1,2-BN cyclohexane is an air- and water-stable compound that cleanly forms a trimer with release of dihydrogen when thermally activated. We also demonstrate that 1,2-BN cyclohexane has a lower activation barrier for ring inversion than cyclohexane due to BN/CC isosterism.

PMID:
21786818
DOI:
10.1021/ja206497x

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