Issue 73, 2012
From the journal:

Chemical Communications

7-Selenabicyclo[2.2.1]heptane†

Phoebe E. Macdougall,ab   Heather M. Aitken,ab   Peter J. Scammells,ac   Yvonne Kavanagh,ab   Sara H. Kyne‡ab  and  Carl H. Schiesser*ab  

* Corresponding authors

a ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Australia

b School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia
E-mail: carlhs@unimelb.edu.au
Fax: +61 3 9347 8189
Tel: +61 3 8344 2432

c Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Victoria, Parkville, Australia

Abstract

Thermolysis of a benzene solution of N-[4-(p-(methoxybenzyl)seleno)cyclohexanoyl]-N,S-dimethyldithiocarbonate affords the hitherto unknown 7-selenabicyclo[2.2.1]heptane in 48% conversion and in 20% yield after chromatography. G3(MP2)-RAD calculations predict a rate constant of 5 × 104 s−1 at 80 °C (3.8 × 106 s−1 at 200 °C) for the intramolecular homolytic substitution process involved in this cyclization.

Graphical abstract: 7-Selenabicyclo[2.2.1]heptane

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Article information

DOI
https://doi.org/10.1039/C2CC34984A
Article type
Communication
Submitted
12 Jul 2012
Accepted
26 Jul 2012
First published
26 Jul 2012

Chem. Commun., 2012,48, 9126-9128

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7-Selenabicyclo[2.2.1]heptane

P. E. Macdougall, H. M. Aitken, P. J. Scammells, Y. Kavanagh, S. H. Kyne and C. H. Schiesser, Chem. Commun., 2012, 48, 9126 DOI: 10.1039/C2CC34984A

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