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Synlett 2005(18): 2832-2834  
DOI: 10.1055/s-2005-918933
LETTER
© Georg Thieme Verlag Stuttgart · New York

Zinc-Mediated Synthesis of Tertiary Alkyl Selenides from Tertiary Alkyl Halides

Alain Krief*a, Michel Derocka,b, Damien Lacroixa,b
a Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, Namur 5000, Belgium
Fax: +32(0)81724536; e-Mail: alain.krief@fundp.ac.be;
b Fonds pour la Formation à la Recherche dans l’Industrie et l’Agriculture, 5 rue d’Egmont, Bruxelles 1000, Belgium
Further Information

Publication History

Received 28 July 2005
Publication Date:
12 October 2005 (online)

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Abstract

Diorganyl selenides are efficiently synthesized from ­tertiary alkyl halides, selenols or selenolates and zinc dibromide as well as from diselenides in the presence of zinc.

Key words

substitution - alkyl halides - diorganyl selenides

    References

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11

As pointed out by a referee ‘an apparent similar reaction was reported recently in the same journal’. [8] The reaction proceeds in polar solvent and has a completely different outcome than that reported in this paper: in MeCN-H2O it gives a different result, demonstrating no significant reaction with tertiary alkyl halides and facile reaction with primary and secondary halides. We are working in order to understand this spectacular solvent effect; less basic solvents usually favor SN1-type reaction.