Issue 21, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Considerations on the stereoselective synthesis of dibrominated spiro-1,3-dioxanes. Synthesis and stereochemistry of monobrominated precursors

Elena Bogdan,a   Ion Grosu,*a   Eugen Mesaros,†a   Loïc Toupet,b   Gerard Plé,c   Sorin Magera  and  Luminita Munteana  

* Corresponding authors

a “Babes-Bolyai” University, Organic Chemistry Department and CSOFSTM, 11 Arany Janos str., Cluj-Napoca, Romania
E-mail: igrosu@chem.ubbcluj.ro

b Université de Rennes I, UMR C6626, France

c Université de Rouen et IRCOF, UPRES-A-6014, Faculté des Sciences de Rouen, Mont Saint Aignan, Cedex, France

Abstract

The synthesis and stereochemistry of monobrominated spiro-1,3-dioxanes, involved as precursors in the diastereoselective synthesis of dibrominated 1,5-dioxaspiro[5.5]undecane derivatives bearing substituents in positions 7, 8 or 9, are reported. The structural aspects are investigated by means of NMR methods and by the molecular structure of two compounds established by single-crystal X-ray diffractometry. The data are used to determine the routes followed by the bromination reactions of spiro-1,3-dioxanes and the asymmetric induction involved in the stereoselectivity of the process.

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Article information

DOI
https://doi.org/10.1039/B004282J
Article type
Paper
Submitted
30 May 2000
Accepted
16 Aug 2000
First published
12 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3635-3639

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Considerations on the stereoselective synthesis of dibrominated spiro-1,3-dioxanes. Synthesis and stereochemistry of monobrominated precursors

E. Bogdan, I. Grosu, E. Mesaros, L. Toupet, G. Plé, S. Mager and L. Muntean, J. Chem. Soc., Perkin Trans. 1, 2000, 3635 DOI: 10.1039/B004282J

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