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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Preparation and Structure of 1,6-Diphenyldispiro[2.1.2.1]octane-4,8-dione

Author(s): Jürgen Voss*, Rüdiger Röske and Gunadi Adiwidjaja

Volume 16, Issue 7, 2019

Page: [535 - 537] Pages: 3

DOI: 10.2174/1570178615666181108103500

Price: $65

Abstract

The dimerization of 1-bromo-2-phenylcyclopropanecarbonyl chloride by the use of the zinc/copper couple selectively leads to anti-trans-1,6-diphenyldispiro[2.1.2.1]octane-4,8-dione, the structure and configuration of which are proved by X-ray structure analysis.

Keywords: Dispiro[2.1.2.1]octane-4, 8-dione, configuration, diastereoselectivity, X-Ray structure, dimerization, diketone.

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[1]
Schmüser, W.; Voss, J. J. Chem Res, 1980, 262-263.
[2]
Röske, R. Systeme mit zwei nicht konjugierten Carbonyl- oder Thiocarbonylgruppen. Darstellung und ESR-spektroskopische Untersuchung ihrer Radikalanionen [Systems with two nonconjugated Carbonyl or Thiocarbonyl Groups. Preparation and ESR Spectroscopic Study of Their Radical Anions]., PhD Thesis, University of Hamburg, Hamburg, Germany. 1989.
[3]
(a)Hoffmann, H.M.R.; Wulff, J-M.; Kütz, A.; Wartchow, R. Angew. Chem., 1982, 94, 79-80.
(b)Haase, K.; Hoffmann, H.M. Angew. Chem. Int. Ed., 1982, 21, 83-84.
[4]
(a)Hoffmann, H.M.R.; Walenta, A.; Eggert, U.; Schomburg, D. Angew. Chem., 1985, 97, 599-600.
(b)Hoffmann, H.M.; Walenta, A.; Eggert, U.; Schomburg, D. Angew. Chem. Int. Ed., 1985, 24, 607-608.
[5]
(a)Wulff, J-M.; Hoffmann, H.M.R. Angew. Chem., 1985, 97, 597-599.
(b)Wulff, J.M.; Hoffmann, H.M. Angew. Chem. Int. Ed., 1985, 24, 605-606.
[6]
Hoffmann, H.M.R.; Geschwinder, P.M.; Hollwege, H.P.; Walenta, A. Helv. Chim. Acta, 1988, 71, 1930-1936.
[7]
Zagidullin, A.A.; Zorin, A.V.; Zorin, V.V. Russ. J. Gen. Chem., 2016, 86, 2307-2311.
[8]
The locants in Fig. 1 and Table 1 result from the X-ray CIF. They deviate from the IUPAC numbering applied for the specification and discussion of atoms in the NMR spectra in S1 and S4.
[9]
Germain, G.; Main, P.; Woolfson, M.M. Acta Crystallogr. Sect A, 1971, 27, 368-376.
[10]
North, A.C.T.; Phillips, D.C.; Mathews, F.S. Acta Crystallogr. Sect A, 1968, 24, 351-359.
[11]
Frenz, B.A. Structure Determination Package; College Station, Texas (USA). , 1982.
[12]
Crystallographic data (excluding structure factors) for 3 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 1582891. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (Fax: +44-(0)1223-336033 or e-mail. deposit@ccdc.cam.ac.uk).

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