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Electrochemical synthesis of a thiophene-containing cyclo[9]pyrrole

Thanh-Tuan Bui1, Adriana Iordache, Zhongrui Chen

  • 1Département de Chimie Moléculaire, UMR 5250 CNRS, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 31, 2012
PubMed

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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