Synthesis and Applications of Stenhouse Salts and Derivatives

Rafael F A Gomes; Jaime A S Coelho; Carlos A M Afonso

doi:10.1002/chem.201705851

Synthesis and Applications of Stenhouse Salts and Derivatives

Chemistry. 2018 Jul 2;24(37):9170-9186. doi: 10.1002/chem.201705851. Epub 2018 Apr 6.

Authors

Rafael F A Gomes¹, Jaime A S Coelho¹, Carlos A M Afonso¹

Affiliation

¹ The Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisboa, Portugal.

PMID: 29393530
DOI: 10.1002/chem.201705851

Abstract

In recent years, Stenhouse salts have attracted much attention as intermediates for the synthesis of cyclopenten-2-enones. This Minireview aims to present an overview of the methods for preparation, further transformation and applications of Stenhouse and Stenhouse-like salts. In this context, the Piancatelli rearrangement and its variants, and the recently reported donor-acceptor Stenhouse salts (DASA) will be addressed. The photophysical properties of DASA and its applications in colorimetric detection of amines, functionalization of polymers for detection of heat and nerve agents, photolithography and orthogonal photoswitching systems are discussed.

Keywords: asymmetric catalysis; carbocycles; fluorescent probes; molecular devices; photochromism.

Publication types

Review