ChemInform Abstract: Syntheses on the Basis of Organo‐Magnesium Compounds of 2,6(7)‐Dibutoxycarbonyltetrathiafulvalene.

Abstract

Starting from the readily available 2,6(7)‐dibutoxycarbonyltetrathiafulvalene (I) the title compounds (III) and (IV) are prepared, which are stable on storage at ‐20 °C in THF.

Bi-TTF, Bis-TTF, and Related TTF Oligomers

“…12 The second synthesis of 1, with spectral characterization, was reported by Neilands and co-workers in 1989 using coupling of the Grignard reagent and decarboxylation (Scheme 1). 13 Thus, the reaction of 5 with butylmagnesium bromide, followed by treatment with bromine or CuBr 2 , produced 6a in 40-56% yield. Transesterification of 6a with KOH in methanol afforded 6b, which was converted into 1 by decarboxylation with LiBr in HMPA.…”

“…For the linearly extended TTF oligomers, Neiland and co-workers first prepared regioisomeric mixtures of trimers and tetramers as byproducts of the synthesis of 6a, but no important properties were reported. 13 Recently, Takimiya and Otsubo prepared a series of dimeric and oligomeric TTFs 46a-g (Scheme 10). 31 Although the oligomers 46b-g comprise various isomeric mixtures due to the E/Z configurations, the structures of these oligomers were well characterized by MS and NMR spectroscopy.…”

Unambiguous Identification of Regioisomeric Tetrathiafulvalenes by Mass Spectrometry: Application to Dihalogeno Derivatives and the First Synthesis of 4,4‘(5‘)-Dichlorotetrathiafulvalene

“…We first attempted its synthesis by a similar approach to that described by Neiland et al. for the preparation of 2f , namely, double lithiation of 2c , followed by treatment with N -chlorosuccinimide. Compound 9 was isolated, but the yields were low and an alternative, more efficient route was sought.…”

Synthesis and Electroconductive Properties of Radical Salts Derived from Tetrathiafulvalene Dimers

“…1 shows two redox waves in benzonitrile, whereas the reported oxidation of 1 in acetonitrile is a three-step process (14,20). By contrast, 2-4 and 5-7 show three redox waves, in which the third redox process seems to be twoelectron oxidation.…”

“…Although bi-TTF 1 was first reported in 1982 as an abstract of a conference, no physical and spectral data were presented (13). The second synthesis of 1 with spectral characterization was reported by Neilands et al in 1989 using copper-catalyzed coupling of the Grignard reagent derived from a TTF diester, followed by decarboxylation with LiBr in HMPA (14). In the course of our studies on the synthesis of functional p-electron systems using transition-metal complexes (15), we planned an efficient synthesis of 1 by the palladium-catalyzed homocoupling of trialkylstannyl-TTF which can be prepared from the commercially available TTF.…”