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INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina
; Fax: (+54) 351-4333030
; Tel: (+54) 351-4334170/73
Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey
; Fax: (+90) 442-2360948
; Tel: (+90) 442-2314405
Org. Biomol. Chem., 2013,11, 955-965
07 Sep 2012,
03 Dec 2012
First published online
04 Dec 2012
The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
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Organic & Biomolecular Chemistry
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