Selective Metalation of 1,3-Dithiole-2-thiones: An Effective Preparation of New Symmetrically and Nonsymmetrically Tetraarylated Tetrathiafulvalenes

Nafe, Julia and Knochel, Paul (2016): Selective Metalation of 1,3-Dithiole-2-thiones: An Effective Preparation of New Symmetrically and Nonsymmetrically Tetraarylated Tetrathiafulvalenes. In: Synthesis-Stuttgart, Vol. 48, No. 1: pp. 103-114

Abstract

We report an efficient preparation of fully functionalized tetrathiafulvalene derivatives (TTF) with an extended -system via a selective magnesiation of 1,3-dithiole-2-thiones (DTT) using 2,2,6,6-tetramethylpiperidin-1-ylmagnesium chloride-lithium chloride (TMPMgClLiCl);subsequent reaction with various electrophiles, such as halides, acid chlorides, allyl bromides, and aryl iodides, smoothly led to new mono- and difunctionalized 1,3-dithiole-2-thione derivatives. A triethyl phosphite mediated cross-coupling of the disubstituted 1,3-dithiole-2-thione derivatives with their oxygen analogues gave access to new symmetrically and nonsymmetrically tetraarylated tetrathiafulvalenes of interest as organic materials.y

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0039-7881
• Language: English