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Thiol-Free E-Selective Approach to Dithiacyclophanes via Ring-Closing Metathesis
Journal
Asian Journal of Organic Chemistry
ISSN
21935807
Date Issued
2023-01-01
Author(s)
Kotha, Sambasivarao
Gupta, Naveen Kumar
Ansari, Saima
Abstract
Application of cyclophanes is well-established in molecular recognition, supramolecular chemistry and material science. Here, we assembled novel [6,6], [8,6] and [6,3,3] dithiacyclophanes by using three facile steps involving potassium thioacetate, Grignard reagent and ring-closing metathesis (RCM). This strategy provides E-isomers of orthometa-, orthopara-, meta- and paradithiacyclophane derivatives selectively by RCM. Sulfur-based precursors (dithiadiformyl compound) are prepared from bromomethyl benzaldehydes instead of thiols as starting materials. The structure of dithiacyclophanes are confirmed unambiguously by single-crystal X-ray diffraction studies and the distinguishing structural features in isomers of cyclophanes are discussed.
Subjects