Regioselective synthesis, X-ray structure, and reactivity of a tricyclic tetrasulfone, 1,3,5,7-tetramethyl-2,4,6,8,9,10-hexathiatricyclo[3.3.1.13,7]decane 2,2,4,4,6,6,8,8-octaoxide, derived from tetramethylhexathiaadamantane

Glen P. Miller; Ingyu Jeon; A. Nikki Faix; Jerry P. Jasinski; Andreas J. Athans; Mark C. Tetreau

doi:10.1039/B004911P

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Regioselective synthesis, X-ray structure, and reactivity of a tricyclic tetrasulfone, 1,3,5,7-tetramethyl-2,4,6,8,9,10-hexathiatricyclo[3.3.1.1^3,7]decane 2,2,4,4,6,6,8,8-octaoxide, derived from tetramethylhexathiaadamantane†

Glen P. Miller,*^a Ingyu Jeon

,‡^a A. Nikki Faix,^a Jerry P. Jasinski,^b Andreas J. Athans^a and Mark C. Tetreau^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of New Hampshire, Durham, USA
E-mail: gpm@cisunix.unh.edu

^b Department of Chemistry, Keene State College, Keene, USA

Abstract

Enthalpically disfavored tetrasulfone 9 is regioselectively synthesized from hexathiaadamantane 1; X-ray crystallographic data shows 9 to be compressed relative to 1 along its transannular S9–S10 through space axis containing sulfide functions; 9 exhibits diverse reactivity including thermal extrusion of SO₂, further oxidation to pentasulfone 10, and transalkylation to tetradodecyl substituted tetrasulfone 11.

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Supplementary files

Analytical data for compounds 1, 7, 9- 11 DOC (409K)

Article information

DOI: https://doi.org/10.1039/B004911P
Article type: Communication
Submitted: 20 Jun 2000
Accepted: 25 Jul 2000
First published: 08 Aug 2000

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J. Chem. Soc., Perkin Trans. 2, 2000, 1777-1780

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Regioselective synthesis, X-ray structure, and reactivity of a tricyclic tetrasulfone, 1,3,5,7-tetramethyl-2,4,6,8,9,10-hexathiatricyclo[3.3.1.1^3,7]decane 2,2,4,4,6,6,8,8-octaoxide, derived from tetramethylhexathiaadamantane

G. P. Miller, I. Jeon<img border="0" src="https://www.rsc.org/images/entities/char_200a.gif" alt=" " xmlns="http://www.rsc.org/schema/rscart38" />, A. N. Faix, J. P. Jasinski, A. J. Athans and M. C. Tetreau, J. Chem. Soc., Perkin Trans. 2, 2000, 1777 DOI: 10.1039/B004911P

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Journal of the Chemical Society, Perkin Transactions 2