Synthesis 2016; 48(06): 845-854
DOI: 10.1055/s-0035-1560400
paper
© Georg Thieme Verlag Stuttgart · New York

Vilsmeier–Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors

Atsushi Fujiokaa, Takashi Kuboa, Miho Watanabea, Masafumi Uedaa, Hisakazu Miyamotoa, Yohji Misaki*a, b
  • aDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
  • bElements Strategy Initiative for Catalysts and Batteries (ESICB), Kyoto University, Katsura, Kyoto 615-8520, Japan
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Publication History

Received: 30 October 2015

Accepted after revision: 14 December 2015

Publication Date:
11 January 2016 (eFirst)

Abstract

The Vilsmeier–Haack type formylations on various 6-aryl-1,4-dithiafulvenes were examined. The furyl derivatives on treatment with an excess of POCl3 in DMF at room temperature mainly afforded dialdehydes substituted at the 6-position and the furan ring, while the thienyl derivatives and the phenyl derivatives mainly gave monoformylated derivatives substituted at the 6-position. The obtained mono- and dialdehydes were converted into monoaryl-substituted 2,2′-ethanediylidene-bis(1,3-dithiole) derivatives and heteroaromatic ring-inserted [3]dendralene derivatives with triple 1,3-dithiol-2-ylidenes and their TTF-fused analogues. Electrochemical properties of the new π-electron donors were also investigated by cyclic voltammetry.

Supporting Information