Lithium 2,3-dihydro-1-benzothiophene-1,1-dioxide: synthesis, characterization, DFT calculations, and reactivity toward aldehydes and azomethines |
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| Authors: | Enzo Cadoni Massimiliano Arca Claudia Fattuoni Maria G. Cabiddu Salvatore Cabiddu |
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| Affiliation: | a Dipartimento di Scienze Chimiche, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato, Italy
b Dipartimento di Chimica Inorganica ed Analitica, Università degli Studi di Cagliari, Cittadella Universitaria di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato, Italy |
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| Abstract: | The sulfonyl carbanion derived from 2,3-dihydro-1-benzothiophene-1,1-dioxide and its lithium salt has been investigated by DFT calculations. NMR and IR spectroscopic analyses showed that the lithium sulfonyl carbanion exists in solution as a monomer in equilibrium with a dimer. The lithium carbanion was treated with aldehydes and azomethynes to give chiral hydroxy and amino derivatives. The stereochemistry of the products and the diastereoselectivity of the reaction were investigated. |
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| Keywords: | Metalation Carbanions Density functional theory calculations Sulfur heterocycles |
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