Chemodivergent Synthesis of 1,4-Benzo[ b ]dithiins and 1,4-Benzodithiafulvenes

Organic Letters 2026 Open access

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Authors: Douglas Bernardo Paixão, Anita B. Kessler, Fabiano S. Rodembusch, Rafael Stieler, Daniel S. Rampon, Paulo H. Schneider
DOI: 10.1021/acs.orglett.5c05364
Cited by: 1
References: 67

Abstract

High Resolution Image Download MS PowerPoint Slide We report a chemodivergent synthesis of 1,4-benzo[ b ]dithiins and 1,4-benzodithiafulvenes from 2-iodoaryl alkynyl sulfides using a NaSH· x H 2 O/KOH system. In DMF, the reaction affords six-membered 1,4-dithiins, whereas in DMSO, these intermediates undergo a base-promoted ring contraction to the corresponding 1,4-dithiafulvenes. Photophysical and mass spectrometry studies support the idea that this chemodivergence arises from the interplay between S 2– /S 3 • – equilibrium and base availability in each solvent, which governs whether the 1,4-dithiin framework is preserved or undergoes ring contraction to 1,4-benzodithiafulvenes.

Fields of Study & Subjects

Sulfur-Based Synthesis Techniques Organic and Molecular Conductors Research Synthesis and Reactivity of Sulfur-Containing Compounds

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
5
Pages
1803–1809
Publication date
27 January 2026
Language
EN