ORTHO-LITHIATION OF PHENYLTHIOETHERS—AND SOME APPLICATIONS
- 1 March 1982
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 12 (3) , 353-356
- https://doi.org/10.1080/03086648208078968
Abstract
A preparative procedure for the ortho-lithiation of phenylthioethers C6H5SR 1 is described. The preparations of 2-alkylthio-substituted benzoic acids 3, benzophenones 5 and phenylphosphines 6 were carried out in isolated yields of 38–73%, depending on reaction and substituent. The procedure provides a simple route to dithiocatechol and trithiopyrogallol derivatives 7 and 8. The ring-lithiation step gives the best results for R = t-C4H9 (80–90%) and R = i-C3H7 (70–80%). R = C2H5 gave lower yields (ca. 45%), while R = CH3 gave principally lithiation at alkyl carbon.Keywords
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