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Issue 6, 2013
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Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions

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Abstract

The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exoanti-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.

Graphical abstract: Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions

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Supplementary files

Article information


Submitted
07 Sep 2012
Accepted
03 Dec 2012
First published
04 Dec 2012

Org. Biomol. Chem., 2013,11, 955-965
Article type
Paper

Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions

K. F. Crespo Andrada, L. E. Peisino, M. Güney, A. Daştan and A. B. Pierini, Org. Biomol. Chem., 2013, 11, 955
DOI: 10.1039/C2OB26768C

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