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Issue 40, 2013
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Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

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Abstract

The fragmentation reaction of differently functionalized [2.2.2]- and [2.2.1]bicyclic systems that leads to substituted five membered heterocycles and five/six membered carbocycles is broadly studied. This reaction is carried out through a retro-Dieckmann-type condensation on strained [2.2.1]bicyclic β-ketosulfones and their counterparts β-ketoesters under very mild catalytic acid or basic conditions and short reaction times. The same reaction is also achieved on [2.2.2]bicyclic β-ketosulfones requiring harsher reaction conditions.

Graphical abstract: Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

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Article information


Submitted
05 Jun 2013
Accepted
19 Aug 2013
First published
19 Aug 2013

Org. Biomol. Chem., 2013,11, 7016-7025
Article type
Paper

Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

E. Moreno-Clavijo, A. J. Moreno-Vargas, A. T. Carmona and I. Robina, Org. Biomol. Chem., 2013, 11, 7016
DOI: 10.1039/C3OB41160E

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